v0.2.13

CHANGELOG.md

@@ -1,5 +1,14 @@
 # RustBox changelog
 
+### 0.2.13
+
+- Added durable per-tenant blob deletion outbox for every configured blob backend (`filesystem` including shared NFS/POSIX, and S3-compatible storage). Attachment metadata deletion and cleanup enqueue now commit atomically, so a temporary storage failure cannot silently orphan blobs.
+- Blob cleanup runs immediately when possible and is also retried by a background worker with claim leases and exponential backoff; missing objects are treated as successful idempotent deletes and retries do not dead-letter permanently.
+- Deleting one attachment, deleting a whole draft, and post-send draft cleanup all use the same durable deletion path. Failed/finalized uploads and failed storage-migration destination objects are queued for cleanup as well.
+- Storage health probes reuse a fixed probe key so a failed cleanup cannot accumulate unbounded health-check objects.
+- Added runtime schema migration V049 for SQLite, MySQL and PostgreSQL (`blob_delete_outbox`). V050 is the next migration number.
+- Bumped the application/source release to 0.2.13.
+
 ### 0.2.12
 
 - Saving or updating a draft no longer raises a realtime “new message” toast/system notification for the Drafts folder; the folder/list still refreshes normally, and IMAP snapshots remain `\Draft` + `\Seen`.

Cargo.lock

@@ -3506,7 +3506,7 @@ dependencies = [
 
 [[package]]
 name = "rustbox"
-version = "0.2.12"
+version = "0.2.13"
 dependencies = [
  "aes-gcm",
  "async-imap",

Cargo.toml

@@ -1,6 +1,6 @@
 [package]
 name = "rustbox"
-version = "0.2.12"
+version = "0.2.13"
 edition = "2024"
 rust-version = "1.99.1"
 default-run = "rustbox"

NOTICE.md

@@ -1,6 +1,6 @@
 # RustBox attribution / notice
 
-RustBox 0.2.12 is derived from the Oxi webmail project:
+RustBox 0.2.13 is derived from the Oxi webmail project:
 
 - Upstream: `c0h1b4/oxi`
 - Base snapshot: `7f1507c486b78cf33e54beb701dd460d3bd2bd5d`

README.md

@@ -1,4 +1,4 @@
-# RustBox 0.2.12
+# RustBox 0.2.13
 
 RustBox is a webmail derived from `c0h1b4/oxi`. The consumed Oxi revision is recorded in `UPSTREAM_BASE`.
 
@@ -34,7 +34,7 @@ rustbox/
 
 `build.rs` combines the CSS modules from `src/web/css/manifest.txt` and JavaScript modules from `src/web/js/manifest.txt`. Cargo embeds the generated CSS/JS bundles, HTML and SVG sprite in the RustBox executable. There is no standalone source `src/web/app.js`; `src/web/` is the single source of truth and Cargo generates the embedded bundles in `OUT_DIR`.
 
-## Storage and search in 0.2.12
+## Storage and search in 0.2.13
 
 RustBox separates three concerns: SQL metadata, blob storage and search. The SQL engine does **not** decide whether `data_dir` may be used. A single-node PostgreSQL/MySQL deployment may still use filesystem blobs and local Tantivy. In cluster mode, local node state is rejected unless the configured backend is explicitly shared.
 
@@ -43,6 +43,8 @@ Blob backends:
 - `storage.backend="filesystem"` — local disk in single-node mode; set `storage.shared=true` only for a real shared POSIX mount such as NFS, CephFS or GlusterFS.
 - `storage.backend="s3"` — AWS S3 or compatible APIs such as MinIO/Ceph RGW.
 
+Physical blob deletion is durable across all blob backends. RustBox records deletion work in the per-account SQL `blob_delete_outbox` in the same transaction that removes attachment metadata, attempts the delete immediately, and retries temporary failures in the background with leases/backoff. This covers local disk, shared POSIX/NFS and S3-compatible storage without permanently dead-lettering failed cleanup.
+
 Search backends:
 
 - `search.backend="local_tantivy"` — single-node.
@@ -166,7 +168,7 @@ rustbox search reindex
 
 Ready Docker examples are in `docker/`: standalone SQLite, PostgreSQL + SILO (S3-compatible) + OpenSearch, and MySQL + NFS + OpenSearch.
 
-All executable application SQL is centralized by dialect under `src/queries/{sqlite,mysql,pgsql}/queries.rs`. The squashed compatibility baseline remains V046; RustBox 0.2.1 adds runtime migration V047 for attachment checksums/logical blob keys and the durable search outbox, while RustBox 0.2.8 adds V048 for monotonic folder-counter generations used by race-safe IMAP counter reconciliation. The next migration number is V049. See `migrations/README.md`.
+All executable application SQL is centralized by dialect under `src/queries/{sqlite,mysql,pgsql}/queries.rs`. The squashed compatibility baseline remains V046; RustBox 0.2.1 adds runtime migration V047 for attachment checksums/logical blob keys and the durable search outbox, RustBox 0.2.8 adds V048 for monotonic folder-counter generations used by race-safe IMAP counter reconciliation, and RustBox 0.2.13 adds V049 for durable blob deletion retries. The next migration number is V050. See `migrations/README.md`.
 
 
 ## Development
@@ -235,7 +237,7 @@ Initialize Git after extracting the release archive:
 ```bash
 git init
 git add .
-git commit -m "RustBox 0.2.12 release"
+git commit -m "RustBox 0.2.13 release"
 ./scripts/setup-upstream.sh
 ```
 

RELEASE-MANIFEST.txt

@@ -1,6 +1,8 @@
-RustBox 0.2.12 release manifest
+RustBox 0.2.13 release manifest
 
-0.2.12 feature/configuration changes:
+0.2.13 feature/configuration changes:
+- adds a durable SQL blob-deletion outbox used by filesystem/shared POSIX/NFS and S3 backends; attachment/draft cleanup is transactionally queued and retried until successful
+- failed finalized uploads and failed destination objects from storage migration are also queued for cleanup; storage health probes reuse a fixed key to avoid unbounded probe-object buildup
 - suppresses realtime “new message” toast/system notifications for Drafts saves while preserving normal folder/list refresh and `\Draft` + `\Seen` IMAP flags
 - adds `Delete draft` in the composer; IMAP deletion is UID/UIDVALIDITY-checked and local draft attachment rows/blobs are cascaded after the server draft is removed
 - adds an explicit `Save draft` action before `Cancel`; it persists the current message and attachments as a real IMAP Drafts snapshot without changing background autosave behavior
@@ -24,7 +26,7 @@ RustBox 0.2.12 release manifest
 - previews PDFs from the authenticated inline attachment endpoint instead of a blob iframe for Safari/iPhone compatibility
 - presents compose attachment/message size limits as compact raw values without implementation-detail descriptions
 - retains the 0.2.9 realtime notification, shortcut and 300-message mailbox behavior
-- requires no runtime schema migration; V049 remains next
+- adds runtime schema migration V049 for durable `blob_delete_outbox`; V050 remains next
 Architecture:
 - database_backend = sqlite | mysql | pgsql selects authoritative SQL only
 - blob storage and search are independent from the SQL engine
@@ -51,7 +53,8 @@ Database/schema:
 - compatibility baseline remains V046
 - runtime migration V047 adds attachment checksum metadata and search_outbox
 - runtime migration V048 adds `folders.counter_generation` for race-safe authoritative IMAP counter writes
-- next migration number: V049
+- runtime migration V049 adds `blob_delete_outbox` for durable physical blob cleanup
+- next migration number: V050
 
 Docker examples:
 - docker/compose-single-sqlite.yml
@@ -61,14 +64,14 @@ Docker examples:
 
 Operations/docs:
 - standalone `scripts/migrate_roundcube.py` imports Roundcube contacts/identities using RustBox config.toml and supports SQLite/MySQL/PostgreSQL targets
-- README.md documents 0.2.12 configuration
+- README.md documents 0.2.13 configuration
 - docker/README.md documents Compose variants
 - docs/STORAGE_SEARCH_OPERATIONS.md documents failure modes, shared-storage requirements and migration behavior
 - TODO.md leaves live SILO/MinIO/AWS/Ceph and real multi-node acceptance validation explicitly pending
 
 Build/release metadata:
 - `scripts/package-release.sh` runs the full Rust release gate before creating ZIP/SHA256 artifacts
-- Cargo.toml version = 0.2.12
+- Cargo.toml version = 0.2.13
 - rust-toolchain.toml pins Rust 1.99.1
 - Cargo.lock is retained for reproducible application builds; the release gate generates it only when missing
 - CI and scripts/build-release.sh use the retained Cargo.lock (generating it only if missing), then run locked tests/Clippy/release build

RELEASE-VALIDATION.txt

@@ -1,6 +1,8 @@
-RustBox 0.2.12 - final source validation
+RustBox 0.2.13 - final source validation
 
-0.2.12 scope:
+0.2.13 scope:
+- durable blob deletion outbox covers filesystem/shared POSIX/NFS and S3, pairing metadata deletion with cleanup enqueue in one SQL transaction and retrying storage failures without permanent dead-lettering
+- failed finalized uploads and failed storage-migration destination objects are queued for cleanup
 - saving/updating a draft stays silent in realtime: Drafts still refreshes, but no “new message” toast/system notification is emitted
 - composer `Delete draft` removes the current verified IMAP draft and cascades local draft attachment metadata/blob cleanup
 - explicit Save draft action before Cancel forces a real IMAP Drafts snapshot while background autosave behavior remains unchanged
@@ -20,17 +22,17 @@ RustBox 0.2.12 - final source validation
 - PDF attachment preview uses the authenticated inline URL for Safari/iPhone compatibility
 - Composing shows only compact attachment/message size-limit values on one line
 - 0.2.9 realtime notification gating, browser shortcut preservation and 300-message defaults remain intact
-- no runtime schema migration is added; V049 remains next
-- version metadata updated to 0.2.12
+- runtime schema migration V049 adds `blob_delete_outbox`; V050 remains next
+- version metadata updated to 0.2.13
 
 Completed in this environment:
-- offline release validator: scripts/validate-release-static.py (374/374 checks passed)
+- offline release validator: scripts/validate-release-static.py (396/396 checks passed)
 - browser JavaScript assembled in manifest order passes `node --check`
 - all JSON files parse successfully
 - Python helper scripts compile successfully
 - shell scripts pass `bash -n`
-- release metadata consistently identifies 0.2.12
-- V048 migration files/catalog registration and SQLite upgrade execution are validated offline
+- release metadata consistently identifies 0.2.13
+- V048/V049 migration files/catalog registration and SQLite upgrade execution are validated offline
 
 
 Not executable in this packaging environment:

config.example.toml

@@ -1,4 +1,4 @@
-# RustBox 0.2.12
+# RustBox 0.2.13
 host = "127.0.0.1"
 port = 3001
 environment = "production"

docs/IMPLEMENTATION_STATUS.md

@@ -1,9 +1,9 @@
-# RustBox 0.2.12 - implementation status
+# RustBox 0.2.13 - implementation status
 
 - Draft saves are realtime-silent: Drafts folder/list updates continue, but saving a draft does not surface as a new-mail notification.
-This file tracks the `0.2.12` source snapshot. Storage/search scope and outstanding acceptance work are tracked in `TODO.md`. A feature is only listed as implemented when working code exists in this source tree; partial items are called out explicitly.
+This file tracks the `0.2.13` source snapshot. Storage/search scope and outstanding acceptance work are tracked in `TODO.md`. A feature is only listed as implemented when working code exists in this source tree; partial items are called out explicitly.
 
-## 0.2.12 browser mail UX
+## 0.2.13 browser mail UX
 
 - Large To/Cc lists collapse to a compact recipient summary and expand on demand.
 - Message pagination exposes both `Load more` and `Load all`; both actions stretch evenly across the full list width, and the reader menu label is shortened to `Details`.
@@ -23,7 +23,8 @@ This file tracks the `0.2.12` source snapshot. Storage/search scope and outstand
 - Composing displays attachment/message size limits as one compact line without configuration/MIME implementation details.
 - Initial synchronization remains silent for new-mail notifications; bulk operations retain one summary toast; browser/system modifier shortcuts remain preserved.
 - Mailbox pages default to 300 messages and the API/preferences accept values up to 300.
-- No runtime schema migration is added; V049 remains next.
+- Blob deletion uses a durable SQL outbox for filesystem/shared POSIX/NFS and S3 backends; attachment/draft metadata deletion is transactionally paired with cleanup enqueue and failed deletes retry in the background.
+- Runtime migration V049 adds `blob_delete_outbox` on SQLite, MySQL and PostgreSQL; V050 is next.
 
 ## 0.2.8 browser security headers
 
@@ -43,7 +44,7 @@ This file tracks the `0.2.12` source snapshot. Storage/search scope and outstand
 - Draft attachment upload/read/delete/snapshot/send paths use the `BlobStorage` abstraction and logical object keys instead of assuming node-local paths.
 - OpenSearch is available as the cluster-capable indexer. Local Tantivy remains single-node only; search may also be disabled.
 - Search mutations use a durable SQL outbox with claim/lease, retry/backoff and dead-letter state; the index remains rebuildable derived state.
-- V047 adds attachment checksum metadata and the search outbox across SQLite, MySQL and PostgreSQL. V048 adds monotonic folder-counter generations used by compare-and-set reconciliation of authoritative IMAP counts; V049 is reserved as the next migration number.
+- V047 adds attachment checksum metadata and the search outbox across SQLite, MySQL and PostgreSQL. V048 adds monotonic folder-counter generations used by compare-and-set reconciliation of authoritative IMAP counts. V049 adds the durable blob deletion outbox; V050 is reserved as the next migration number.
 - SQL global-schema initialization is centralized in `db::pool::configure()`; database-backed sessions do not repeat startup DDL for SQLite, MySQL or PostgreSQL.
 - Docker Compose examples cover standalone SQLite, PostgreSQL + SILO (S3-compatible) + OpenSearch, and MySQL + NFS + OpenSearch.
 - Live SILO/MinIO/AWS S3/Ceph RGW, live NFS multi-host, live OpenSearch and full multi-node failover acceptance remain release-environment validation items and are not represented as completed here.

docs/RELEASING.md

@@ -26,7 +26,7 @@ RUSTBOX_CONFIG=./config.dev.toml ./target/release/rustbox --check-config
 
 Browser JavaScript source lives in functional modules under `src/web/js/`, ordered by `src/web/js/manifest.txt`. `build.rs` concatenates those modules into the embedded `rustbox-ui.js` asset during every Cargo build. The repository has no duplicate `ui/` snapshot; `src/web/` is the only browser UI source.
 
-## Updating an existing checkout to 0.2.12
+## Updating an existing checkout to 0.2.13
 
 Do not overlay the release with `cp *` or another command that skips dotfiles. That can retain stale `.github`, `.env.example`, or `Cargo.lock` files.
 

docs/STORAGE_SEARCH_OPERATIONS.md

@@ -1,6 +1,6 @@
-# RustBox 0.2.12 storage/search operations
+# RustBox 0.2.13 storage/search operations
 
-RustBox 0.2.12 treats SQL, blob storage and search as independent capabilities. The database engine does not decide whether `data_dir` is allowed.
+RustBox 0.2.13 treats SQL, blob storage and search as independent capabilities. The database engine does not decide whether `data_dir` is allowed.
 
 ## Deployment matrix
 
@@ -28,6 +28,12 @@ For NFS/CephFS/GlusterFS:
 
 Attachment SQL rows store logical object keys. This keeps SQL independent from a node-specific filesystem path.
 
+## Durable blob deletion
+
+Attachment deletion is not best-effort. RustBox writes a `blob_delete_outbox` entry in the same SQL transaction that removes the attachment row or draft row, then attempts the physical delete immediately. A background worker retries failures with claim leases and exponential backoff until the object is gone; object-store `NotFound` is treated as success. The same path is used for local filesystem, shared POSIX/NFS and S3-compatible backends. Failed finalized uploads and failed migration destination objects are also queued for cleanup.
+
+This avoids orphan accumulation when storage is temporarily unavailable while also avoiding the inverse failure mode where a blob is deleted first and the SQL transaction later fails.
+
 ## Search and outbox
 
 OpenSearch is the cluster-capable indexer. Every indexed document is scoped by `user_hash`; queries add a server-side tenant filter and deterministic document IDs are routed by tenant.

migrations/README.md

@@ -1,6 +1,6 @@
 # Database schemas and migrations
 
-RustBox 0.2.12 keeps SQL, blob storage and search as independent concerns:
+RustBox 0.2.13 keeps SQL, blob storage and search as independent concerns:
 
 ```text
 database_backend = sqlite | mysql | pgsql
@@ -18,18 +18,21 @@ migrations/
 ├── sqlite/
 │   ├── schema.sql
 │   ├── V047__blob_keys_and_search_outbox.sql
-│   └── V048__folder_counter_generation.sql
+│   ├── V048__folder_counter_generation.sql
+│   └── V049__blob_delete_outbox.sql
 ├── mysql/
 │   ├── schema.sql
 │   ├── V047__blob_keys_and_search_outbox.sql
-│   └── V048__folder_counter_generation.sql
+│   ├── V048__folder_counter_generation.sql
+│   └── V049__blob_delete_outbox.sql
 └── pgsql/
     ├── schema.sql
     ├── V047__blob_keys_and_search_outbox.sql
-    └── V048__folder_counter_generation.sql
+    ├── V048__folder_counter_generation.sql
+    └── V049__blob_delete_outbox.sql
 ```
 
-Each `schema.sql` is the current complete schema for fresh installations. The historical compatibility baseline remains **V046**. RustBox 0.2.1 adds **V047**, which adds attachment SHA-256 metadata and the durable search outbox used by external indexing. RustBox 0.2.8 adds **V048**, which adds the monotonic `folders.counter_generation` used to reject stale IMAP counter writes even when the numeric counts temporarily return to an earlier value.
+Each `schema.sql` is the current complete schema for fresh installations. The historical compatibility baseline remains **V046**. RustBox 0.2.1 adds **V047**, which adds attachment SHA-256 metadata and the durable search outbox used by external indexing. RustBox 0.2.8 adds **V048**, which adds the monotonic `folders.counter_generation` used to reject stale IMAP counter writes even when the numeric counts temporarily return to an earlier value. RustBox 0.2.13 adds **V049**, the durable `blob_delete_outbox` used to retry physical object deletion after metadata is removed.
 
 Account data is isolated inside the selected physical database with a deterministic, collision-checked table prefix derived from the account hash. The `{{p}}` marker in tenant SQL is replaced by RustBox at provisioning/migration time. Sessions are global and therefore are not prefixed.
 
@@ -37,7 +40,7 @@ Account data is isolated inside the selected physical database with a determinis
 
 Every schema-changing release must add the same logical migration for all supported SQL engines and register it in `src/db/pool.rs`. Do not update only `schema.sql`: fresh installs use the baseline while existing installations use the numbered migration path.
 
-RustBox 0.2.12 does not add a runtime schema migration; **V049** remains the next migration number.
+RustBox 0.2.13 adds runtime migration **V049** on SQLite, MySQL and PostgreSQL. **V050** is the next migration number.
 
 Redis and Redis Sentinel do not use SQL migrations.
 

migrations/mysql/V049__blob_delete_outbox.sql

@@ -0,0 +1,11 @@
+CREATE TABLE {{p}}blob_delete_outbox (
+    id VARCHAR(64) PRIMARY KEY,
+    storage_key TEXT NOT NULL,
+    attempts BIGINT NOT NULL DEFAULT 0,
+    available_at BIGINT NOT NULL DEFAULT 0,
+    claimed_until BIGINT NOT NULL DEFAULT 0,
+    last_error TEXT NULL,
+    created_at BIGINT NOT NULL,
+    updated_at BIGINT NOT NULL,
+    INDEX idx_blob_delete_outbox_ready (available_at, claimed_until, updated_at)
+) ENGINE=InnoDB DEFAULT CHARSET=utf8mb4 COLLATE=utf8mb4_unicode_ci;

migrations/mysql/schema.sql

@@ -1,7 +1,7 @@
 -- RustBox 0.2.0 MySQL schema.
 -- One physical database contains global sessions plus isolated per-account tables.
 -- Application tables are materialized by replacing {{p}} with a collision-checked prefix.
--- Squashed compatibility baseline: V046. Current runtime schema: V048.
+-- Squashed compatibility baseline: V046. Current runtime schema: V049.
 
 -- RUSTBOX:GLOBAL-BEGIN
 CREATE TABLE IF NOT EXISTS rustbox_accounts (
@@ -190,6 +190,19 @@ CREATE TABLE {{p}}draft_attachments (
     created_at VARCHAR(64) NOT NULL DEFAULT (CAST(CURRENT_TIMESTAMP AS CHAR))
 ) ENGINE=InnoDB DEFAULT CHARSET=utf8mb4 COLLATE=utf8mb4_unicode_ci;
 
+
+CREATE TABLE {{p}}blob_delete_outbox (
+    id VARCHAR(64) PRIMARY KEY,
+    storage_key TEXT NOT NULL,
+    attempts BIGINT NOT NULL DEFAULT 0,
+    available_at BIGINT NOT NULL DEFAULT 0,
+    claimed_until BIGINT NOT NULL DEFAULT 0,
+    last_error TEXT NULL,
+    created_at BIGINT NOT NULL,
+    updated_at BIGINT NOT NULL,
+    INDEX idx_blob_delete_outbox_ready (available_at, claimed_until, updated_at)
+) ENGINE=InnoDB DEFAULT CHARSET=utf8mb4 COLLATE=utf8mb4_unicode_ci;
+
 CREATE TABLE {{p}}search_outbox (
     id VARCHAR(64) PRIMARY KEY,
     generation VARCHAR(64) NOT NULL,

migrations/pgsql/V049__blob_delete_outbox.sql

@@ -0,0 +1,13 @@
+CREATE TABLE {{p}}blob_delete_outbox (
+    id TEXT PRIMARY KEY,
+    storage_key TEXT NOT NULL,
+    attempts BIGINT NOT NULL DEFAULT 0,
+    available_at BIGINT NOT NULL DEFAULT 0,
+    claimed_until BIGINT NOT NULL DEFAULT 0,
+    last_error TEXT,
+    created_at BIGINT NOT NULL,
+    updated_at BIGINT NOT NULL
+);
+
+CREATE INDEX {{p}}idx_blob_delete_outbox_ready
+    ON {{p}}blob_delete_outbox(available_at, claimed_until, updated_at);

migrations/pgsql/schema.sql

@@ -1,7 +1,7 @@
 -- RustBox 0.2.0 PostgreSQL schema.
 -- One physical database contains global sessions plus isolated per-account tables.
 -- Application tables are materialized by replacing {{p}} with a collision-checked prefix.
--- Squashed compatibility baseline: V046. Current runtime schema: V048.
+-- Squashed compatibility baseline: V046. Current runtime schema: V049.
 
 -- RUSTBOX:GLOBAL-BEGIN
 CREATE TABLE IF NOT EXISTS rustbox_accounts (
@@ -190,6 +190,20 @@ CREATE TABLE {{p}}draft_attachments (
     created_at TEXT NOT NULL DEFAULT (CURRENT_TIMESTAMP::text)
 );
 
+
+CREATE TABLE {{p}}blob_delete_outbox (
+    id TEXT PRIMARY KEY,
+    storage_key TEXT NOT NULL,
+    attempts BIGINT NOT NULL DEFAULT 0,
+    available_at BIGINT NOT NULL DEFAULT 0,
+    claimed_until BIGINT NOT NULL DEFAULT 0,
+    last_error TEXT,
+    created_at BIGINT NOT NULL,
+    updated_at BIGINT NOT NULL
+);
+
+CREATE INDEX {{p}}idx_blob_delete_outbox_ready ON {{p}}blob_delete_outbox(available_at, claimed_until, updated_at);
+
 CREATE TABLE {{p}}search_outbox (
     id TEXT PRIMARY KEY,
     generation TEXT NOT NULL,

migrations/sqlite/V049__blob_delete_outbox.sql

@@ -0,0 +1,13 @@
+CREATE TABLE {{p}}blob_delete_outbox (
+    id TEXT PRIMARY KEY,
+    storage_key TEXT NOT NULL,
+    attempts INTEGER NOT NULL DEFAULT 0,
+    available_at INTEGER NOT NULL DEFAULT 0,
+    claimed_until INTEGER NOT NULL DEFAULT 0,
+    last_error TEXT,
+    created_at INTEGER NOT NULL,
+    updated_at INTEGER NOT NULL
+);
+
+CREATE INDEX {{p}}idx_blob_delete_outbox_ready
+    ON {{p}}blob_delete_outbox(available_at, claimed_until, updated_at);

migrations/sqlite/schema.sql

@@ -1,7 +1,7 @@
 -- RustBox 0.2.0 SQLite schema.
 -- One physical database contains global sessions plus isolated per-account tables.
 -- Application tables are materialized from the tenant section by replacing {{p}}.
--- Squashed compatibility baseline: V046. Current runtime schema: V048.
+-- Squashed compatibility baseline: V046. Current runtime schema: V049.
 
 -- RUSTBOX:GLOBAL-BEGIN
 CREATE TABLE IF NOT EXISTS rustbox_accounts (
@@ -136,6 +136,20 @@ CREATE TABLE {{p}}draft_attachments (
     FOREIGN KEY (draft_id) REFERENCES {{p}}drafts(id) ON DELETE CASCADE
 );
 
+
+CREATE TABLE {{p}}blob_delete_outbox (
+    id TEXT PRIMARY KEY,
+    storage_key TEXT NOT NULL,
+    attempts INTEGER NOT NULL DEFAULT 0,
+    available_at INTEGER NOT NULL DEFAULT 0,
+    claimed_until INTEGER NOT NULL DEFAULT 0,
+    last_error TEXT,
+    created_at INTEGER NOT NULL,
+    updated_at INTEGER NOT NULL
+);
+
+CREATE INDEX {{p}}idx_blob_delete_outbox_ready ON {{p}}blob_delete_outbox(available_at, claimed_until, updated_at);
+
 CREATE TABLE {{p}}search_outbox (
     id TEXT PRIMARY KEY,
     generation TEXT NOT NULL,

packaging/rustbox.toml

@@ -1,4 +1,4 @@
-# RustBox 0.2.12 - packaged production configuration (DEB/RPM)
+# RustBox 0.2.13 - packaged production configuration (DEB/RPM)
 #
 # This file contains all supported RustBox configuration options.
 # Commented options are optional and do not change the packaged defaults.

scripts/validate-release-static.py

@@ -1,5 +1,5 @@
 #!/usr/bin/env python3
-"""Static/offline release checks for RustBox 0.2.12.
+"""Static/offline release checks for RustBox 0.2.13.
 
 These checks intentionally avoid pretending to replace `cargo test`: they validate
 configuration, SQL migrations, Docker examples, query-catalog parity and release
@@ -49,14 +49,14 @@ def extract_section(text: str, begin: str, end: str) -> str:
 
 # Release/toolchain metadata.
 cargo = tomllib.loads(read("Cargo.toml"))
-require(cargo["package"]["version"] == "0.2.12", "Cargo package version is 0.2.12")
+require(cargo["package"]["version"] == "0.2.13", "Cargo package version is 0.2.13")
 require(cargo["package"]["rust-version"] == "1.99.1", "Cargo rust-version is 1.99.1")
 toolchain = tomllib.loads(read("rust-toolchain.toml"))
 require(toolchain["toolchain"]["channel"] == "1.99.1", "rust-toolchain pins Rust 1.99.1")
 require((ROOT / "Cargo.lock").is_file(), "Cargo.lock is retained for reproducible application builds")
 lock = tomllib.loads(read("Cargo.lock"))
 lock_rustbox = next((pkg for pkg in lock.get("package", []) if pkg.get("name") == "rustbox"), {})
-require(lock_rustbox.get("version") == "0.2.12", "Cargo.lock RustBox package version is 0.2.12")
+require(lock_rustbox.get("version") == "0.2.13", "Cargo.lock RustBox package version is 0.2.13")
 require(cargo["dependencies"].get("encoding_rs") == "0.8", "direct charset decoder dependency is pinned")
 require("encoding_rs" in lock_rustbox.get("dependencies", []), "Cargo.lock records direct charset decoder dependency")
 require("cargo generate-lockfile" in read("scripts/build-release.sh"), "release script generates Cargo.lock when missing")
@@ -71,10 +71,10 @@ require("make_zip.py" in package_script and "sha256sum" in package_script, "rele
 require("cargo generate-lockfile" in read(".github/workflows/ci.yml"), "CI regenerates Cargo.lock before --locked checks")
 require("validate-release-static.py" in read("scripts/build-release.sh"), "release script runs offline/static release gate")
 require("validate-release-static.py" in read(".github/workflows/ci.yml"), "CI runs offline/static release gate")
-require(read("README.md").startswith("# RustBox 0.2.12"), "README identifies RustBox 0.2.12")
-require(read("RELEASE-MANIFEST.txt").startswith("RustBox 0.2.12"), "release manifest identifies RustBox 0.2.12")
-require(read("RELEASE-VALIDATION.txt").startswith("RustBox 0.2.12"), "release validation identifies RustBox 0.2.12")
-require(read("docs/IMPLEMENTATION_STATUS.md").startswith("# RustBox 0.2.12"), "implementation status identifies RustBox 0.2.12")
+require(read("README.md").startswith("# RustBox 0.2.13"), "README identifies RustBox 0.2.13")
+require(read("RELEASE-MANIFEST.txt").startswith("RustBox 0.2.13"), "release manifest identifies RustBox 0.2.13")
+require(read("RELEASE-VALIDATION.txt").startswith("RustBox 0.2.13"), "release validation identifies RustBox 0.2.13")
+require(read("docs/IMPLEMENTATION_STATUS.md").startswith("# RustBox 0.2.13"), "implementation status identifies RustBox 0.2.13")
 bootstrap_js = read("src/web/js/00-bootstrap.js")
 bindings_js = read("src/web/js/95-bindings-boot.js")
 realtime_js = read("src/web/js/80-settings-realtime.js")
@@ -124,8 +124,8 @@ require('encoding_rs::Encoding::for_label' in read("src/imap/parse.rs") and 'dec
 require('let is_pdf = response_content_type_is(&response, "application/pdf");' in read("src/routes/mod.rs") and 'HeaderValue::from_static("SAMEORIGIN")' in read("src/routes/mod.rs") and "HeaderValue::from_static(\"frame-ancestors 'self'\")" in read("src/routes/mod.rs"), "security headers allow same-origin framing for inline PDF previews only")
 index_html = read("src/web/index.html")
 require('class="compose-limit-summary"' in index_html and 'Per-file upload limit set with' not in index_html and 'Hard limit for the complete RFC822/MIME message' not in index_html, "Composing shows compact raw size limits without implementation details")
-require("V048" in read("RELEASE-MANIFEST.txt") and "V049" in read("RELEASE-MANIFEST.txt"), "release manifest documents V048 and reserves V049")
-require("V048" in read("migrations/README.md") and "V049" in read("migrations/README.md"), "migration guide documents V048 and reserves V049")
+require("V049" in read("RELEASE-MANIFEST.txt") and "V050" in read("RELEASE-MANIFEST.txt"), "release manifest documents V049 and reserves V050")
+require("V049" in read("migrations/README.md") and "V050" in read("migrations/README.md"), "migration guide documents V049 and reserves V050")
 require((ROOT / "docs/STORAGE_SEARCH_OPERATIONS.md").is_file(), "storage/search operations guide exists")
 require('imap_host = ""' not in read("config.dev.toml"), "development config does not override IMAP host with an invalid empty value")
 require(not re.search(r"(?m)^IMAP_HOST=\s*$", read(".env.example")), "environment example does not set an invalid empty IMAP host")
@@ -521,6 +521,10 @@ try:
     require(outbox is not None, "fresh SQLite schema has search_outbox")
     outbox_columns = {row[1] for row in conn.execute("PRAGMA table_info(u_test__search_outbox)")}
     require("claimed_until" in outbox_columns, "fresh SQLite search_outbox separates worker lease from retry availability")
+    blob_outbox = conn.execute("SELECT 1 FROM sqlite_master WHERE type='table' AND name='u_test__blob_delete_outbox'").fetchone()
+    require(blob_outbox is not None, "fresh SQLite schema has blob_delete_outbox")
+    blob_outbox_columns = {row[1] for row in conn.execute("PRAGMA table_info(u_test__blob_delete_outbox)")}
+    require({"storage_key", "attempts", "available_at", "claimed_until", "last_error"}.issubset(blob_outbox_columns), "fresh SQLite blob deletion outbox has retry/lease state")
     folder_columns = {row[1] for row in conn.execute("PRAGMA table_info(u_test__folders)")}
     require("counter_generation" in folder_columns, "fresh SQLite schema has V048 folder counter generation")
     sqlite_header_sync = "INSERT INTO u_test__user_meta (key, value) VALUES ('header_sync_generation', '1') ON CONFLICT(key) DO UPDATE SET value = CAST(value AS INTEGER) + 1"
@@ -595,12 +599,26 @@ try:
 except Exception as exc:
     errors.append(f"SQLite V048 migration execution failed: {exc}")
 
+# V049 creates the durable blob deletion outbox.
+try:
+    conn = sqlite3.connect(":memory:")
+    migration = read("migrations/sqlite/V049__blob_delete_outbox.sql").replace("{{p}}", "u_test__")
+    conn.executescript(migration)
+    columns = {row[1] for row in conn.execute("PRAGMA table_info(u_test__blob_delete_outbox)")}
+    require({"id", "storage_key", "attempts", "available_at", "claimed_until", "last_error", "created_at", "updated_at"}.issubset(columns), "V049 creates SQLite blob_delete_outbox with durable retry state")
+    indexes = {row[1] for row in conn.execute("PRAGMA index_list(u_test__blob_delete_outbox)")}
+    require(any("blob_delete_outbox_ready" in name for name in indexes), "V049 creates SQLite blob cleanup readiness index")
+    conn.close()
+except Exception as exc:
+    errors.append(f"SQLite V049 migration execution failed: {exc}")
+
 # Migration/query parity across SQL engines.
 for dialect in ("sqlite", "mysql", "pgsql"):
     require((ROOT / f"migrations/{dialect}/V047__blob_keys_and_search_outbox.sql").is_file(), f"V047 migration exists for {dialect}")
     require((ROOT / f"migrations/{dialect}/V048__folder_counter_generation.sql").is_file(), f"V048 migration exists for {dialect}")
+    require((ROOT / f"migrations/{dialect}/V049__blob_delete_outbox.sql").is_file(), f"V049 migration exists for {dialect}")
     schema_text = read(f"migrations/{dialect}/schema.sql")
-    require("Current runtime schema: V048" in schema_text and "counter_generation" in schema_text, f"fresh {dialect} schema includes V048 folder counter generation")
+    require("Current runtime schema: V049" in schema_text and "counter_generation" in schema_text and "blob_delete_outbox" in schema_text, f"fresh {dialect} schema includes V049 blob deletion outbox")
     queries = read(f"src/queries/{dialect}/queries.rs")
     folder_block = re.search(r"pub mod db_folders\s*\{(.*?)\n\}", queries, re.S)
     require(folder_block is not None and "Q_032" in folder_block.group(1) and "counter_generation = counter_generation + 1" in folder_block.group(1), f"folder counter CAS increments generation for {dialect}")
@@ -609,11 +627,17 @@ for dialect in ("sqlite", "mysql", "pgsql"):
     if block_match:
         qnames = set(re.findall(r"pub const (Q_\d{3})", block_match.group(1)))
         require(qnames == {f"Q_{i:03d}" for i in range(1, 8)}, f"search outbox Q001-Q007 parity for {dialect}")
+    blob_block = re.search(r"pub mod db_blob_delete_outbox\s*\{(.*?)\n\}", queries, re.S)
+    require(blob_block is not None, f"blob deletion outbox query module exists for {dialect}")
+    if blob_block:
+        blob_qnames = set(re.findall(r"pub const (Q_\d{3})", blob_block.group(1)))
+        require(blob_qnames == {f"Q_{i:03d}" for i in range(1, 6)}, f"blob deletion outbox Q001-Q005 parity for {dialect}")
 
 pool = read("src/db/pool.rs")
 for dialect in ("SQLITE", "MYSQL", "PGSQL"):
     require(f"{dialect}_MIGRATIONS" in pool and "V047__blob_keys_and_search_outbox.sql" in pool, f"runtime migration catalog includes V047 ({dialect.lower()})")
     require(f"{dialect}_MIGRATIONS" in pool and "V048__folder_counter_generation.sql" in pool, f"runtime migration catalog includes V048 ({dialect.lower()})")
+    require(f"{dialect}_MIGRATIONS" in pool and "V049__blob_delete_outbox.sql" in pool, f"runtime migration catalog includes V049 ({dialect.lower()})")
 require("const BASE_SCHEMA_VERSION: u32 = 46" in pool, "legacy squashed baseline stays V046")
 require("latest_schema_version" in pool, "runtime schema version is computed from migrations")
 require(
@@ -706,9 +730,9 @@ require("storage.shared" in config_rs, "cluster-safe shared POSIX storage is cap
 require("AmazonS3Builder" in storage_rs and "BufWriter" in storage_rs, "S3 backend uses streaming object-store writer")
 require("with_retry" in storage_rs and "with_checksum_algorithm" in storage_rs, "S3 backend configures retries and checksums")
 require("attachment_key" in storage_rs and "users/{user_hash}/drafts/{draft_id}/attachments/{attachment_id}" in storage_rs, "attachments use logical storage keys")
-require("destination.delete(&target_key).await" in storage_rs, "attachment migration removes a failed destination blob after verification failure")
+require("enqueue_unreferenced_delete(&conn, destination.as_ref(), &target_key).await" in storage_rs, "attachment migration durably queues failed destination blob cleanup")
 require("let _ = upload.abort().await" in storage_rs and "failed reading source" in storage_rs, "attachment migration aborts a destination upload if source streaming fails")
-require("if let Err(error) = crate::db::drafts::update_attachment_storage" in storage_rs, "attachment migration removes destination object when SQL pointer update fails")
+require("if let Err(error) = crate::db::drafts::update_attachment_storage" in storage_rs and "Failed to queue storage migration cleanup" in storage_rs, "attachment migration queues destination cleanup when SQL pointer update fails")
 require("OpenSearchBackend" in search_rs, "OpenSearch backend is implemented")
 require("reqwest::blocking" not in search_rs and 'features = ["json", "rustls-tls"]' in read("Cargo.toml"), "OpenSearch uses the async reqwest client without blocking feature")
 require("async fn request(" in search_rs and "request.send().await" in search_rs, "OpenSearch HTTP requests are asynchronous")
@@ -717,6 +741,15 @@ require("process_search_outbox" in search_rs and "claim(&conn" in search_rs, "Op
 require("fn event_lease_secs(&self) -> u64" in search_rs and "let lease_secs = backend.event_lease_secs();" in search_rs and "claim(&conn, &event, 60)" not in search_rs, "OpenSearch outbox lease is derived from HTTP timeout/failover budget instead of a fixed 60 seconds")
 require("opensearch_event_lease_covers_timeout_and_failover_budget" in search_rs, "OpenSearch lease budget has a source-level unit regression test")
 require("claimed_until" in read("migrations/sqlite/V047__blob_keys_and_search_outbox.sql") and "reenqueue_preserves_active_claim_lease" in read("src/db/search_outbox.rs"), "outbox re-enqueue cannot steal an active worker lease")
+blob_delete_rs = read("src/db/blob_delete_outbox.rs")
+attachments_rs = read("src/routes/attachments.rs")
+send_rs = read("src/routes/send.rs")
+require("mark_failure" in blob_delete_rs and "min(3600)" in blob_delete_rs and "max_attempts" not in blob_delete_rs and "dead_letter" not in read("migrations/sqlite/V049__blob_delete_outbox.sql"), "blob deletion outbox retries indefinitely with capped backoff and no permanent dead-letter")
+require("unchecked_transaction()" in attachments_rs and "blob_delete_outbox::enqueue(&transaction" in attachments_rs and "delete_draft_attachment(&transaction" in attachments_rs, "single attachment deletion atomically queues blob cleanup with metadata deletion")
+require("blob_delete_outbox::enqueue(&transaction" in drafts_rs and "delete_draft(&transaction" in drafts_rs, "whole-draft deletion atomically queues every attachment blob before metadata cascade")
+require("blob_delete_outbox::enqueue(&transaction" in send_rs and "delete_draft(&transaction" in send_rs, "post-send draft cleanup atomically queues attachment blobs")
+require("start_blob_delete_worker" in storage_rs and "process_blob_delete_outbox" in storage_rs and "start_blob_delete_worker(config.clone(), storage.clone())" in read("src/main.rs"), "durable blob deletion worker is wired at startup")
+require('let key = "_health/probe".to_string();' in storage_rs, "storage health probe uses a fixed key and cannot accumulate unique orphan probe objects")
 require("index_messages_batch_with_connection" in search_rs and "enqueue_upsert_on" in search_rs, "OpenSearch outbox supports caller-owned SQL transactions")
 require("enqueue_participates_in_caller_transaction" in read("src/db/search_outbox.rs"), "transactional outbox rollback has a unit test")
 require("search reindex" in read("README.md") and "run_search_reindex" in read("src/main.rs"), "full search reindex command is documented and wired")
@@ -734,19 +767,25 @@ require("docs/RUSTBOX_PLAN.md" not in read("docs/IMPLEMENTATION_STATUS.md"), "im
 require("intentionally run one RustBox application container" in read("docker/README.md"), "Docker docs distinguish shared backing topology from multi-app load balancing")
 
 attachments_rs = read("src/routes/attachments.rs")
-require(".begin_upload(&key)" in attachments_rs and ".get(&attachment.storage_key)" in attachments_rs and (".delete(&attachment.storage_key)" in attachments_rs or ".delete(&storage_key)" in attachments_rs), "attachment HTTP routes use BlobStorage")
+require(".begin_upload(&key)" in attachments_rs and ".get(&attachment.storage_key)" in attachments_rs and "storage::process_queued_delete" in attachments_rs, "attachment HTTP routes use BlobStorage")
 require("tokio::fs::" not in attachments_rs, "attachment HTTP routes no longer access local filesystem directly")
-attachment_db_delete = attachments_rs.find("db::drafts::delete_draft_attachment")
-attachment_blob_delete = attachments_rs.find("storage.delete(&storage_key)", attachment_db_delete)
-require(attachment_db_delete >= 0 and attachment_blob_delete > attachment_db_delete, "attachment delete commits DB removal before best-effort blob cleanup")
+attachment_enqueue = attachments_rs.find("blob_delete_outbox::enqueue(&transaction")
+attachment_db_delete = attachments_rs.find("delete_draft_attachment(&transaction", attachment_enqueue)
+attachment_commit = attachments_rs.find(".commit()", attachment_db_delete)
+attachment_blob_delete = attachments_rs.find("storage::process_queued_delete", attachment_commit)
+require(0 <= attachment_enqueue < attachment_db_delete < attachment_commit < attachment_blob_delete, "attachment delete commits metadata removal and cleanup enqueue atomically before physical blob deletion")
 drafts_rs = read("src/routes/drafts.rs")
-draft_db_delete = drafts_rs.find("db::drafts::delete_draft(&conn, &id)")
-draft_blob_delete = drafts_rs.find("storage.delete(&attachment.storage_key)", draft_db_delete)
-require(draft_db_delete >= 0 and draft_blob_delete > draft_db_delete, "draft delete commits DB removal before best-effort blob cleanup")
+draft_enqueue = drafts_rs.find("blob_delete_outbox::enqueue(&transaction")
+draft_db_delete = drafts_rs.find("delete_draft(&transaction", draft_enqueue)
+draft_commit = drafts_rs.find(".commit()", draft_db_delete)
+draft_blob_delete = drafts_rs.find("storage::process_queued_delete", draft_commit)
+require(0 <= draft_enqueue < draft_db_delete < draft_commit < draft_blob_delete, "draft delete commits metadata cascade and cleanup enqueue atomically before physical blob deletion")
 send_rs = read("src/routes/send.rs")
-send_db_delete = send_rs.find("db::drafts::delete_draft(&conn, draft_id)")
-send_blob_delete = send_rs.find("storage.delete(&attachment.storage_key)", send_db_delete)
-require(send_db_delete >= 0 and send_blob_delete > send_db_delete, "post-send cleanup commits DB removal before best-effort blob cleanup")
+send_enqueue = send_rs.find("blob_delete_outbox::enqueue(&transaction")
+send_db_delete = send_rs.find("delete_draft(&transaction", send_enqueue)
+send_commit = send_rs.find("transaction.commit()", send_db_delete)
+send_blob_delete = send_rs.find("storage::process_queued_delete", send_commit)
+require(0 <= send_enqueue < send_db_delete < send_commit < send_blob_delete, "post-send cleanup commits metadata removal and cleanup enqueue atomically before physical blob deletion")
 
 # Repository/source-package hygiene independent of Cargo.
 source_files = [path for path in ROOT.rglob("*") if path.is_file() and ".git" not in path.parts and "target" not in path.parts]

src/db/blob_delete_outbox.rs

@@ -0,0 +1,155 @@
+use std::time::{SystemTime, UNIX_EPOCH};
+
+use crate::db::pool::{Connection, params};
+
+#[derive(Debug, Clone)]
+pub struct BlobDeleteEvent {
+    pub id: String,
+    pub storage_key: String,
+    pub attempts: u32,
+}
+
+pub fn now_epoch() -> i64 {
+    SystemTime::now()
+        .duration_since(UNIX_EPOCH)
+        .unwrap_or_default()
+        .as_secs()
+        .min(i64::MAX as u64) as i64
+}
+
+pub fn enqueue(conn: &Connection, storage_key: &str) -> Result<BlobDeleteEvent, String> {
+    if storage_key.trim().is_empty() {
+        return Err("cannot enqueue an empty blob storage key".to_string());
+    }
+    let id = uuid::Uuid::new_v4().to_string();
+    let now = now_epoch();
+    let result = match crate::db::pool::configured_backend() {
+        crate::db::pool::DatabaseBackend::Mysql => conn.execute(
+            crate::dbq!(db_blob_delete_outbox::Q_001),
+            params![&id, storage_key, now, now],
+        ),
+        _ => conn.execute(
+            crate::dbq!(db_blob_delete_outbox::Q_001),
+            params![&id, storage_key, now],
+        ),
+    };
+    result.map_err(|e| format!("failed to enqueue blob deletion: {e}"))?;
+    Ok(BlobDeleteEvent {
+        id,
+        storage_key: storage_key.to_string(),
+        attempts: 0,
+    })
+}
+
+pub fn list_ready(conn: &Connection, limit: usize) -> Result<Vec<BlobDeleteEvent>, String> {
+    let now = now_epoch();
+    let mut stmt = conn
+        .prepare(crate::dbq!(db_blob_delete_outbox::Q_002))
+        .map_err(|e| format!("failed to prepare blob deletion outbox query: {e}"))?;
+    let query_params = match crate::db::pool::configured_backend() {
+        crate::db::pool::DatabaseBackend::Mysql => params![now, now, limit],
+        _ => params![now, limit],
+    };
+    let rows = stmt
+        .query_map(query_params, |row| {
+            Ok(BlobDeleteEvent {
+                id: row.get(0)?,
+                storage_key: row.get(1)?,
+                attempts: row.get::<_, i64>(2)?.max(0) as u32,
+            })
+        })
+        .map_err(|e| format!("failed to query blob deletion outbox: {e}"))?;
+    rows.map(|row| row.map_err(|e| format!("failed to read blob deletion outbox row: {e}")))
+        .collect()
+}
+
+pub fn claim(conn: &Connection, event: &BlobDeleteEvent, lease_secs: u64) -> Result<bool, String> {
+    let now = now_epoch();
+    let lease_until = now.saturating_add(lease_secs.max(1) as i64);
+    let changed = match crate::db::pool::configured_backend() {
+        crate::db::pool::DatabaseBackend::Mysql => conn.execute(
+            crate::dbq!(db_blob_delete_outbox::Q_003),
+            params![lease_until, &event.id, now, now],
+        ),
+        _ => conn.execute(
+            crate::dbq!(db_blob_delete_outbox::Q_003),
+            params![&event.id, lease_until, now],
+        ),
+    }
+    .map_err(|e| format!("failed to claim blob deletion: {e}"))?;
+    Ok(changed > 0)
+}
+
+pub fn mark_success(conn: &Connection, event: &BlobDeleteEvent) -> Result<bool, String> {
+    let changed = conn
+        .execute(
+            crate::dbq!(db_blob_delete_outbox::Q_004),
+            params![&event.id],
+        )
+        .map_err(|e| format!("failed to acknowledge blob deletion: {e}"))?;
+    Ok(changed > 0)
+}
+
+pub fn mark_failure(
+    conn: &Connection,
+    event: &BlobDeleteEvent,
+    error: &str,
+) -> Result<bool, String> {
+    let attempts = event.attempts.saturating_add(1);
+    let backoff = 2u64.saturating_pow(attempts.min(12)).min(3600);
+    let available_at = now_epoch().saturating_add(backoff as i64);
+    let now = now_epoch();
+    let truncated: String = error.chars().take(2048).collect();
+    let changed = match crate::db::pool::configured_backend() {
+        crate::db::pool::DatabaseBackend::Mysql => conn.execute(
+            crate::dbq!(db_blob_delete_outbox::Q_005),
+            params![attempts, available_at, &truncated, now, &event.id],
+        ),
+        _ => conn.execute(
+            crate::dbq!(db_blob_delete_outbox::Q_005),
+            params![&event.id, attempts, available_at, &truncated, now],
+        ),
+    }
+    .map_err(|e| format!("failed to update blob deletion retry state: {e}"))?;
+    Ok(changed > 0)
+}
+
+#[cfg(test)]
+mod tests {
+    use super::*;
+    use crate::db::pool::open_test_db;
+
+    #[test]
+    fn enqueue_participates_in_caller_transaction() {
+        let conn = open_test_db();
+        {
+            let transaction = conn.unchecked_transaction().unwrap();
+            enqueue(&transaction, "users/test/drafts/d/attachments/a").unwrap();
+        }
+        assert!(list_ready(&conn, 10).unwrap().is_empty());
+    }
+
+    #[test]
+    fn failed_deletions_are_retried_instead_of_dead_lettered() {
+        let conn = open_test_db();
+        let event = enqueue(&conn, "users/test/drafts/d/attachments/a").unwrap();
+        assert!(claim(&conn, &event, 60).unwrap());
+        assert!(mark_failure(&conn, &event, "storage unavailable").unwrap());
+        let count: i64 = conn
+            .query_row(
+                "SELECT COUNT(*) FROM blob_delete_outbox WHERE id=?1",
+                params![&event.id],
+                |row| row.get(0),
+            )
+            .unwrap();
+        assert_eq!(count, 1);
+    }
+
+    #[test]
+    fn successful_delete_is_acknowledged() {
+        let conn = open_test_db();
+        let event = enqueue(&conn, "users/test/drafts/d/attachments/a").unwrap();
+        assert!(mark_success(&conn, &event).unwrap());
+        assert!(list_ready(&conn, 10).unwrap().is_empty());
+    }
+}

src/db/drafts.rs

@@ -257,6 +257,67 @@ pub fn get_draft_attachments(
     Ok(attachments)
 }
 
+pub fn lock_draft_for_update(conn: &Connection, id: &str) -> Result<bool, String> {
+    match conn.query_row(crate::dbq!(db_drafts::Q_010), params![id], |_row| Ok(())) {
+        Ok(()) => Ok(true),
+        Err(crate::db::pool::DbError::QueryReturnedNoRows) => Ok(false),
+        Err(e) => Err(format!("Failed to lock draft: {e}")),
+    }
+}
+
+pub fn get_draft_attachment_for_update(
+    conn: &Connection,
+    draft_id: &str,
+    attachment_id: &str,
+) -> Result<Option<DraftAttachment>, String> {
+    let result = conn.query_row(
+        crate::dbq!(db_drafts::Q_011),
+        params![draft_id, attachment_id],
+        |row| {
+            Ok(DraftAttachment {
+                id: row.get(0)?,
+                draft_id: row.get(1)?,
+                filename: row.get(2)?,
+                content_type: row.get(3)?,
+                size: row.get(4)?,
+                storage_key: row.get(5)?,
+                checksum_sha256: row.get(6)?,
+                created_at: row.get(7)?,
+            })
+        },
+    );
+    match result {
+        Ok(attachment) => Ok(Some(attachment)),
+        Err(crate::db::pool::DbError::QueryReturnedNoRows) => Ok(None),
+        Err(e) => Err(format!("Failed to lock draft attachment: {e}")),
+    }
+}
+
+pub fn get_draft_attachments_for_update(
+    conn: &Connection,
+    draft_id: &str,
+) -> Result<Vec<DraftAttachment>, String> {
+    let mut stmt = conn
+        .prepare(crate::dbq!(db_drafts::Q_012))
+        .map_err(|e| format!("Failed to prepare locked draft attachments query: {e}"))?;
+    let rows = stmt
+        .query_map(params![draft_id], |row| {
+            Ok(DraftAttachment {
+                id: row.get(0)?,
+                draft_id: row.get(1)?,
+                filename: row.get(2)?,
+                content_type: row.get(3)?,
+                size: row.get(4)?,
+                storage_key: row.get(5)?,
+                checksum_sha256: row.get(6)?,
+                created_at: row.get(7)?,
+            })
+        })
+        .map_err(|e| format!("Failed to query locked draft attachments: {e}"))?;
+    rows.map(|row| row.map_err(|e| format!("Failed to read locked attachment row: {e}")))
+        .collect()
+}
+
 pub fn delete_draft_attachment(conn: &Connection, id: &str) -> Result<bool, String> {
     let deleted = conn
         .execute(crate::dbq!(db_drafts::Q_008), params![id])

src/db/mod.rs

@@ -1,3 +1,4 @@
+pub mod blob_delete_outbox;
 pub mod calendar;
 pub mod contact_groups;
 pub mod contacts;

src/db/pool.rs

@@ -30,6 +30,10 @@ const SQLITE_MIGRATIONS: &[(u32, &str)] = &[
         48,
         include_str!("../../migrations/sqlite/V048__folder_counter_generation.sql"),
     ),
+    (
+        49,
+        include_str!("../../migrations/sqlite/V049__blob_delete_outbox.sql"),
+    ),
 ];
 const MYSQL_MIGRATIONS: &[(u32, &str)] = &[
     (
@@ -40,6 +44,10 @@ const MYSQL_MIGRATIONS: &[(u32, &str)] = &[
         48,
         include_str!("../../migrations/mysql/V048__folder_counter_generation.sql"),
     ),
+    (
+        49,
+        include_str!("../../migrations/mysql/V049__blob_delete_outbox.sql"),
+    ),
 ];
 const PGSQL_MIGRATIONS: &[(u32, &str)] = &[
     (
@@ -50,9 +58,14 @@ const PGSQL_MIGRATIONS: &[(u32, &str)] = &[
         48,
         include_str!("../../migrations/pgsql/V048__folder_counter_generation.sql"),
     ),
+    (
+        49,
+        include_str!("../../migrations/pgsql/V049__blob_delete_outbox.sql"),
+    ),
 ];
 
 const TENANT_TABLES: &[&str] = &[
+    "blob_delete_outbox",
     "calendar_events",
     "calendar_settings",
     "contact_group_members",
@@ -83,6 +96,7 @@ const TENANT_TABLES: &[&str] = &[
 ];
 
 const IMPORT_TABLES: &[&str] = &[
+    "blob_delete_outbox",
     "calendar_events",
     "calendar_settings",
     "contact_groups",

src/main.rs

@@ -121,6 +121,8 @@ async fn main() -> Result<(), Box<dyn std::error::Error>> {
             .map_err(std::io::Error::other)?;
     }
     let _search_worker = search_engine.start_worker();
+    let _blob_delete_worker =
+        crate::storage::start_blob_delete_worker(config.clone(), storage.clone());
 
     let event_bus = Arc::new(realtime::events::EventBus::new());
     let idle_manager = Arc::new(realtime::idle::IdleManager::new());

src/queries/mysql/queries.rs

@@ -167,6 +167,9 @@ pub mod db_drafts {
     pub const Q_008: &str = "DELETE FROM draft_attachments WHERE id = ?";
     pub const Q_009: &str =
         "UPDATE draft_attachments SET file_path=?, checksum_sha256=? WHERE id=?";
+    pub const Q_010: &str = "SELECT id FROM drafts WHERE id=? FOR UPDATE";
+    pub const Q_011: &str = "SELECT id, draft_id, filename, content_type, size, file_path, checksum_sha256, created_at FROM draft_attachments WHERE draft_id=? AND id=? FOR UPDATE";
+    pub const Q_012: &str = "SELECT id, draft_id, filename, content_type, size, file_path, checksum_sha256, created_at FROM draft_attachments WHERE draft_id=? ORDER BY created_at ASC FOR UPDATE";
 }
 
 pub mod db_folder_preferences {
@@ -527,3 +530,11 @@ pub mod db_search_outbox {
     pub const Q_006: &str = "UPDATE search_outbox SET claimed_until=? WHERE id=? AND generation=? AND dead_letter=0 AND available_at <= ? AND claimed_until <= ?";
     pub const Q_007: &str = "DELETE FROM search_outbox WHERE updated_at < ?";
 }
+
+pub mod db_blob_delete_outbox {
+    pub const Q_001: &str = "INSERT INTO blob_delete_outbox (id, storage_key, attempts, available_at, claimed_until, last_error, created_at, updated_at) VALUES (?, ?, 0, 0, 0, NULL, ?, ?)";
+    pub const Q_002: &str = "SELECT id, storage_key, attempts FROM blob_delete_outbox WHERE available_at <= ? AND claimed_until <= ? ORDER BY updated_at ASC LIMIT ?";
+    pub const Q_003: &str = "UPDATE blob_delete_outbox SET claimed_until=? WHERE id=? AND available_at <= ? AND claimed_until <= ?";
+    pub const Q_004: &str = "DELETE FROM blob_delete_outbox WHERE id=?";
+    pub const Q_005: &str = "UPDATE blob_delete_outbox SET attempts=?, available_at=?, claimed_until=0, last_error=?, updated_at=? WHERE id=?";
+}

src/queries/pgsql/queries.rs

@@ -168,6 +168,9 @@ pub mod db_drafts {
     pub const Q_008: &str = "DELETE FROM draft_attachments WHERE id = $1";
     pub const Q_009: &str =
         "UPDATE draft_attachments SET file_path=$1, checksum_sha256=$2 WHERE id=$3";
+    pub const Q_010: &str = "SELECT id FROM drafts WHERE id=$1 FOR UPDATE";
+    pub const Q_011: &str = "SELECT id, draft_id, filename, content_type, size, file_path, checksum_sha256, created_at FROM draft_attachments WHERE draft_id=$1 AND id=$2 FOR UPDATE";
+    pub const Q_012: &str = "SELECT id, draft_id, filename, content_type, size, file_path, checksum_sha256, created_at FROM draft_attachments WHERE draft_id=$1 ORDER BY created_at ASC FOR UPDATE";
 }
 
 pub mod db_folder_preferences {
@@ -528,3 +531,11 @@ pub mod db_search_outbox {
     pub const Q_006: &str = "UPDATE search_outbox SET claimed_until=$3 WHERE id=$1 AND generation=$2 AND dead_letter=0 AND available_at <= $4 AND claimed_until <= $4";
     pub const Q_007: &str = "DELETE FROM search_outbox WHERE updated_at < $1";
 }
+
+pub mod db_blob_delete_outbox {
+    pub const Q_001: &str = "INSERT INTO blob_delete_outbox (id, storage_key, attempts, available_at, claimed_until, last_error, created_at, updated_at) VALUES ($1, $2, 0, 0, 0, NULL, $3, $3)";
+    pub const Q_002: &str = "SELECT id, storage_key, attempts FROM blob_delete_outbox WHERE available_at <= $1 AND claimed_until <= $1 ORDER BY updated_at ASC LIMIT $2";
+    pub const Q_003: &str = "UPDATE blob_delete_outbox SET claimed_until=$2 WHERE id=$1 AND available_at <= $3 AND claimed_until <= $3";
+    pub const Q_004: &str = "DELETE FROM blob_delete_outbox WHERE id=$1";
+    pub const Q_005: &str = "UPDATE blob_delete_outbox SET attempts=$2, available_at=$3, claimed_until=0, last_error=$4, updated_at=$5 WHERE id=$1";
+}

src/queries/sqlite/queries.rs

@@ -165,6 +165,9 @@ pub mod db_drafts {
     pub const Q_008: &str = "DELETE FROM draft_attachments WHERE id = ?1";
     pub const Q_009: &str =
         "UPDATE draft_attachments SET file_path=?1, checksum_sha256=?2 WHERE id=?3";
+    pub const Q_010: &str = "SELECT id FROM drafts WHERE id=?1";
+    pub const Q_011: &str = "SELECT id, draft_id, filename, content_type, size, file_path, checksum_sha256, created_at FROM draft_attachments WHERE draft_id=?1 AND id=?2";
+    pub const Q_012: &str = "SELECT id, draft_id, filename, content_type, size, file_path, checksum_sha256, created_at FROM draft_attachments WHERE draft_id=?1 ORDER BY created_at ASC";
 }
 
 pub mod db_folder_preferences {
@@ -782,3 +785,11 @@ pub mod db_search_outbox {
     pub const Q_006: &str = "UPDATE search_outbox SET claimed_until=?3 WHERE id=?1 AND generation=?2 AND dead_letter=0 AND available_at <= ?4 AND claimed_until <= ?4";
     pub const Q_007: &str = "DELETE FROM search_outbox WHERE updated_at < ?1";
 }
+
+pub mod db_blob_delete_outbox {
+    pub const Q_001: &str = "INSERT INTO blob_delete_outbox (id, storage_key, attempts, available_at, claimed_until, last_error, created_at, updated_at) VALUES (?1, ?2, 0, 0, 0, NULL, ?3, ?3)";
+    pub const Q_002: &str = "SELECT id, storage_key, attempts FROM blob_delete_outbox WHERE available_at <= ?1 AND claimed_until <= ?1 ORDER BY updated_at ASC LIMIT ?2";
+    pub const Q_003: &str = "UPDATE blob_delete_outbox SET claimed_until=?2 WHERE id=?1 AND available_at <= ?3 AND claimed_until <= ?3";
+    pub const Q_004: &str = "DELETE FROM blob_delete_outbox WHERE id=?1";
+    pub const Q_005: &str = "UPDATE blob_delete_outbox SET attempts=?2, available_at=?3, claimed_until=0, last_error=?4, updated_at=?5 WHERE id=?1";
+}

src/routes/attachments.rs

@@ -11,7 +11,7 @@ use crate::auth::session::SessionState;
 use crate::config::AppConfig;
 use crate::db;
 use crate::error::AppError;
-use crate::storage::{BlobStorage, attachment_key};
+use crate::storage::{self, BlobStorage, attachment_key};
 
 #[derive(Debug, Serialize)]
 struct UploadResponse {
@@ -73,7 +73,13 @@ pub async fn upload_attachment(
             let chunk = match field.chunk().await {
                 Ok(chunk) => chunk,
                 Err(e) => {
-                    let _ = writer.abort().await;
+                    if writer.abort().await.is_err()
+                        && let Err(cleanup_error) =
+                            storage::enqueue_unreferenced_delete(&conn, storage.as_ref(), &key)
+                                .await
+                    {
+                        tracing::error!(error = %cleanup_error, storage_key = %key, "Failed to queue aborted attachment cleanup");
+                    }
                     return Err(AppError::BadRequest(format!(
                         "Failed to read field data: {e}"
                     )));
@@ -82,7 +88,12 @@ pub async fn upload_attachment(
             let Some(chunk) = chunk else { break };
             size = size.saturating_add(chunk.len());
             if size > max_attachment_size {
-                let _ = writer.abort().await;
+                if writer.abort().await.is_err()
+                    && let Err(cleanup_error) =
+                        storage::enqueue_unreferenced_delete(&conn, storage.as_ref(), &key).await
+                {
+                    tracing::error!(error = %cleanup_error, storage_key = %key, "Failed to queue oversized attachment cleanup");
+                }
                 return Err(AppError::BadRequest(format!(
                     "File '{}' exceeds maximum size of {} MiB",
                     filename, config.max_attachment_size_mb
@@ -90,18 +101,37 @@ pub async fn upload_attachment(
             }
             checksum.update(&chunk);
             if let Err(e) = writer.write(chunk).await {
-                let _ = writer.abort().await;
+                if writer.abort().await.is_err()
+                    && let Err(cleanup_error) =
+                        storage::enqueue_unreferenced_delete(&conn, storage.as_ref(), &key).await
+                {
+                    tracing::error!(error = %cleanup_error, storage_key = %key, "Failed to queue interrupted attachment cleanup");
+                }
                 return Err(AppError::ServiceUnavailable(format!(
                     "Failed to upload attachment: {e}"
                 )));
             }
         }
 
-        let stat = writer.finish().await.map_err(|e| {
-            AppError::ServiceUnavailable(format!("Failed to finalize attachment upload: {e}"))
-        })?;
+        let stat = match writer.finish().await {
+            Ok(stat) => stat,
+            Err(e) => {
+                if let Err(cleanup_error) =
+                    storage::enqueue_unreferenced_delete(&conn, storage.as_ref(), &key).await
+                {
+                    tracing::error!(error = %cleanup_error, storage_key = %key, "Failed to queue failed-finalize attachment cleanup");
+                }
+                return Err(AppError::ServiceUnavailable(format!(
+                    "Failed to finalize attachment upload: {e}"
+                )));
+            }
+        };
         if stat.size != size as u64 {
-            let _ = storage.delete(&key).await;
+            if let Err(cleanup_error) =
+                storage::enqueue_unreferenced_delete(&conn, storage.as_ref(), &key).await
+            {
+                tracing::error!(error = %cleanup_error, storage_key = %key, "Failed to queue invalid attachment cleanup");
+            }
             return Err(AppError::InternalError(format!(
                 "Attachment size verification failed for '{filename}'"
             )));
@@ -118,7 +148,11 @@ pub async fn upload_attachment(
             checksum_sha256: Some(&checksum),
         };
         if let Err(e) = db::drafts::add_draft_attachment(&conn, &attachment) {
-            let _ = storage.delete(&key).await;
+            if let Err(cleanup_error) =
+                storage::enqueue_unreferenced_delete(&conn, storage.as_ref(), &key).await
+            {
+                tracing::error!(error = %cleanup_error, storage_key = %key, "Failed to queue unattached blob cleanup");
+            }
             return Err(AppError::InternalError(e));
         }
 
@@ -180,21 +214,30 @@ pub async fn delete_attachment(
     let conn = db::pool::open_user_db(&config.data_dir, &session.user_hash)
         .map_err(|e| AppError::InternalError(format!("Failed to open database: {e}")))?;
 
-    let attachments =
-        db::drafts::get_draft_attachments(&conn, &draft_id).map_err(AppError::InternalError)?;
-    let attachment = attachments
-        .iter()
-        .find(|a| a.id == attachment_id)
+    let transaction = conn.unchecked_transaction().map_err(|e| {
+        AppError::InternalError(format!(
+            "Failed to start attachment delete transaction: {e}"
+        ))
+    })?;
+    let attachment =
+        db::drafts::get_draft_attachment_for_update(&transaction, &draft_id, &attachment_id)
+            .map_err(AppError::InternalError)?
             .ok_or_else(|| AppError::NotFound("Attachment not found".to_string()))?;
-
     let storage_key = attachment.storage_key.clone();
-    let deleted = db::drafts::delete_draft_attachment(&conn, &attachment_id)
+    let cleanup_event = db::blob_delete_outbox::enqueue(&transaction, &storage_key)
+        .map_err(AppError::InternalError)?;
+    let deleted = db::drafts::delete_draft_attachment(&transaction, &attachment_id)
         .map_err(AppError::InternalError)?;
     if !deleted {
         return Err(AppError::NotFound("Attachment not found".to_string()));
     }
-    if let Err(error) = storage.delete(&storage_key).await {
-        tracing::warn!(error = %error, storage_key = %storage_key, "Failed to remove deleted attachment blob");
+    transaction.commit().map_err(|e| {
+        AppError::InternalError(format!("Failed to commit attachment deletion: {e}"))
+    })?;
+    if let Err(error) =
+        storage::process_queued_delete(&conn, storage.as_ref(), &cleanup_event).await
+    {
+        tracing::warn!(error = %error, storage_key = %storage_key, "Failed to process queued attachment blob deletion");
     }
 
     Ok(Json(DeleteResponse {

src/routes/drafts.rs

@@ -1179,25 +1179,44 @@ pub async fn delete_draft_handler(
             delete_imap_draft_source(imap_client.as_ref(), &creds, &drafts_folder, source).await?;
     }
 
-    let attachments = if existing.is_some() {
-        db::drafts::get_draft_attachments(&conn, &id).map_err(AppError::InternalError)?
-    } else {
-        Vec::new()
-    };
-    if existing.is_some() {
-        let deleted = db::drafts::delete_draft(&conn, &id).map_err(AppError::InternalError)?;
+    let (attachments, cleanup_events) = if existing.is_some() {
+        let transaction = conn.unchecked_transaction().map_err(|e| {
+            AppError::InternalError(format!("Failed to start draft delete transaction: {e}"))
+        })?;
+        if !db::drafts::lock_draft_for_update(&transaction, &id).map_err(AppError::InternalError)? {
+            return Err(AppError::NotFound("Draft not found".to_string()));
+        }
+        let attachments = db::drafts::get_draft_attachments_for_update(&transaction, &id)
+            .map_err(AppError::InternalError)?;
+        let mut events = Vec::with_capacity(attachments.len());
+        for attachment in &attachments {
+            events.push(
+                db::blob_delete_outbox::enqueue(&transaction, &attachment.storage_key)
+                    .map_err(AppError::InternalError)?,
+            );
+        }
+        let deleted =
+            db::drafts::delete_draft(&transaction, &id).map_err(AppError::InternalError)?;
         if !deleted {
             return Err(AppError::NotFound("Draft not found".to_string()));
         }
-    }
+        transaction.commit().map_err(|e| {
+            AppError::InternalError(format!("Failed to commit draft deletion: {e}"))
+        })?;
+        (attachments, events)
+    } else {
+        (Vec::new(), Vec::new())
+    };
+
     let mut attachments_deleted = 0usize;
-    for attachment in &attachments {
-        match storage.delete(&attachment.storage_key).await {
-            Ok(()) => attachments_deleted += 1,
+    for (attachment, event) in attachments.iter().zip(cleanup_events.iter()) {
+        match storage::process_queued_delete(&conn, storage.as_ref(), event).await {
+            Ok(true) => attachments_deleted += 1,
+            Ok(false) => {}
             Err(error) => tracing::warn!(
                 error = %error,
                 storage_key = %attachment.storage_key,
-                "Failed to remove deleted draft attachment blob"
+                "Failed to process queued draft attachment deletion"
             ),
         }
     }

src/routes/send.rs

@@ -457,26 +457,65 @@ async fn load_draft_attachments(
 }
 
 async fn cleanup_draft(data_dir: &str, user_hash: &str, draft_id: &str, storage: &dyn BlobStorage) {
-    let Ok(conn) = db::pool::open_user_db(data_dir, user_hash) else {
+    let conn = match db::pool::open_user_db(data_dir, user_hash) {
+        Ok(conn) => conn,
+        Err(error) => {
+            tracing::warn!(error = %error, "Failed to open database for draft cleanup after send");
             return;
+        }
     };
-    let attachments = db::drafts::get_draft_attachments(&conn, draft_id).unwrap_or_default();
-    let deleted = match db::drafts::delete_draft(&conn, draft_id) {
+    let transaction = match conn.unchecked_transaction() {
+        Ok(transaction) => transaction,
+        Err(error) => {
+            tracing::warn!(error = %error, "Failed to start draft cleanup transaction after send");
+            return;
+        }
+    };
+    match db::drafts::lock_draft_for_update(&transaction, draft_id) {
+        Ok(true) => {}
+        Ok(false) => return,
+        Err(error) => {
+            tracing::warn!(error = %error, "Failed to lock draft for cleanup after send");
+            return;
+        }
+    }
+    let attachments = match db::drafts::get_draft_attachments_for_update(&transaction, draft_id) {
+        Ok(attachments) => attachments,
+        Err(error) => {
+            tracing::warn!(error = %error, "Failed to load draft attachments for cleanup after send");
+            return;
+        }
+    };
+    let mut cleanup_events = Vec::with_capacity(attachments.len());
+    for attachment in &attachments {
+        match db::blob_delete_outbox::enqueue(&transaction, &attachment.storage_key) {
+            Ok(event) => cleanup_events.push(event),
+            Err(error) => {
+                tracing::warn!(error = %error, storage_key = %attachment.storage_key, "Failed to queue draft attachment cleanup after send");
+                return;
+            }
+        }
+    }
+    let deleted = match db::drafts::delete_draft(&transaction, draft_id) {
         Ok(deleted) => deleted,
-        Err(e) => {
-            tracing::warn!(error = %e, "Failed to delete draft after send");
+        Err(error) => {
+            tracing::warn!(error = %error, "Failed to delete draft after send");
             return;
         }
     };
     if !deleted {
         return;
     }
-    for attachment in attachments {
-        if let Err(e) = storage.delete(&attachment.storage_key).await {
+    if let Err(error) = transaction.commit() {
+        tracing::warn!(error = %error, "Failed to commit draft cleanup after send");
+        return;
+    }
+    for (attachment, event) in attachments.iter().zip(cleanup_events.iter()) {
+        if let Err(error) = storage::process_queued_delete(&conn, storage, event).await {
             tracing::warn!(
-                error = %e,
+                error = %error,
                 storage_key = %attachment.storage_key,
-                "Failed to delete draft attachment after send"
+                "Failed to process queued draft attachment cleanup after send"
             );
         }
     }

src/storage/mod.rs

@@ -160,13 +160,17 @@ impl BlobStorage for ObjectStorage {
     }
 
     async fn health(&self) -> Result<(), String> {
-        let key = format!("_health/{}", uuid::Uuid::new_v4());
+        let key = "_health/probe".to_string();
         let mut upload = self.begin_upload(&key).await?;
         upload.write(Bytes::from_static(b"ok")).await?;
         let stat = upload.finish().await?;
         if stat.size != 2 {
-            let _ = self.delete(&key).await;
-            return Err("storage health probe returned unexpected size".to_string());
+            return match self.delete(&key).await {
+                Ok(()) => Err("storage health probe returned unexpected size".to_string()),
+                Err(cleanup_error) => Err(format!(
+                    "storage health probe returned unexpected size and cleanup failed: {cleanup_error}"
+                )),
+            };
         }
         self.delete(&key).await?;
         Ok(())
@@ -311,6 +315,89 @@ pub fn from_config(config: &AppConfig) -> Result<Arc<dyn BlobStorage>, String> {
     }
 }
 
+const BLOB_DELETE_BATCH_SIZE: usize = 100;
+const BLOB_DELETE_LEASE_SECS: u64 = 60;
+const BLOB_DELETE_WORKER_INTERVAL_SECS: u64 = 30;
+
+pub async fn process_queued_delete(
+    conn: &crate::db::pool::Connection,
+    storage: &dyn BlobStorage,
+    event: &crate::db::blob_delete_outbox::BlobDeleteEvent,
+) -> Result<bool, String> {
+    if !crate::db::blob_delete_outbox::claim(conn, event, BLOB_DELETE_LEASE_SECS)? {
+        return Ok(false);
+    }
+    match storage.delete(&event.storage_key).await {
+        Ok(()) => {
+            crate::db::blob_delete_outbox::mark_success(conn, event)?;
+            Ok(true)
+        }
+        Err(error) => {
+            crate::db::blob_delete_outbox::mark_failure(conn, event, &error)?;
+            tracing::warn!(
+                error = %error,
+                storage_key = %event.storage_key,
+                attempts = event.attempts.saturating_add(1),
+                "Blob deletion failed; cleanup remains queued"
+            );
+            Ok(false)
+        }
+    }
+}
+
+pub async fn enqueue_unreferenced_delete(
+    conn: &crate::db::pool::Connection,
+    storage: &dyn BlobStorage,
+    storage_key: &str,
+) -> Result<bool, String> {
+    match crate::db::blob_delete_outbox::enqueue(conn, storage_key) {
+        Ok(event) => process_queued_delete(conn, storage, &event).await,
+        Err(queue_error) => match storage.delete(storage_key).await {
+            Ok(()) => Ok(true),
+            Err(delete_error) => Err(format!(
+                "failed to persist blob cleanup ({queue_error}); direct delete also failed: {delete_error}"
+            )),
+        },
+    }
+}
+
+pub async fn process_blob_delete_outbox(
+    config: &AppConfig,
+    storage: &dyn BlobStorage,
+) -> Result<usize, String> {
+    let mut processed = 0usize;
+    for user_hash in crate::db::pool::list_account_user_hashes()? {
+        let conn = crate::db::pool::open_user_db(&config.data_dir, &user_hash)?;
+        let events = crate::db::blob_delete_outbox::list_ready(&conn, BLOB_DELETE_BATCH_SIZE)?;
+        for event in events {
+            if process_queued_delete(&conn, storage, &event).await? {
+                processed = processed.saturating_add(1);
+            }
+        }
+    }
+    Ok(processed)
+}
+
+pub fn start_blob_delete_worker(
+    config: Arc<AppConfig>,
+    storage: Arc<dyn BlobStorage>,
+) -> tokio::task::JoinHandle<()> {
+    tokio::spawn(async move {
+        loop {
+            match process_blob_delete_outbox(&config, storage.as_ref()).await {
+                Ok(processed) if processed > 0 => {
+                    tracing::debug!(processed, "Processed queued blob deletions");
+                }
+                Ok(_) => {}
+                Err(error) => {
+                    tracing::warn!(%error, "Blob deletion worker pass failed");
+                }
+            }
+            tokio::time::sleep(Duration::from_secs(BLOB_DELETE_WORKER_INTERVAL_SECS)).await;
+        }
+    })
+}
+
 pub async fn read_all(storage: &dyn BlobStorage, key: &str) -> Result<Vec<u8>, String> {
     let mut stream = storage.get(key).await?;
     let mut data = Vec::new();
@@ -537,7 +624,11 @@ pub async fn migrate_attachments(
                 let source_checksum = format!("{:x}", hasher.finalize());
                 let target_stat = upload.finish().await?;
                 if target_stat.size != source_meta.len() {
-                    let _ = destination.delete(&target_key).await;
+                    if let Err(cleanup_error) =
+                        enqueue_unreferenced_delete(&conn, destination.as_ref(), &target_key).await
+                    {
+                        eprintln!("fail {target_key}: cleanup queue failed: {cleanup_error}");
+                    }
                     report.failed += 1;
                     eprintln!("fail {target_key}: size verification failed");
                     continue;
@@ -548,14 +639,29 @@ pub async fn migrate_attachments(
                     {
                         Ok(checksum) => checksum,
                         Err(error) => {
-                            let _ = destination.delete(&target_key).await;
+                            if let Err(cleanup_error) = enqueue_unreferenced_delete(
+                                &conn,
+                                destination.as_ref(),
+                                &target_key,
+                            )
+                            .await
+                            {
+                                eprintln!(
+                                    "fail {target_key}: cleanup queue failed: {cleanup_error}"
+                                );
+                            }
                             report.failed += 1;
                             eprintln!("fail {target_key}: checksum verification failed: {error}");
                             continue;
                         }
                     };
                     if target_checksum != source_checksum {
-                        let _ = destination.delete(&target_key).await;
+                        if let Err(cleanup_error) =
+                            enqueue_unreferenced_delete(&conn, destination.as_ref(), &target_key)
+                                .await
+                        {
+                            eprintln!("fail {target_key}: cleanup queue failed: {cleanup_error}");
+                        }
                         report.failed += 1;
                         eprintln!("fail {target_key}: checksum verification failed");
                         continue;
@@ -567,7 +673,11 @@ pub async fn migrate_attachments(
                     &target_key,
                     Some(&source_checksum),
                 ) {
-                    let _ = destination.delete(&target_key).await;
+                    if let Err(cleanup_error) =
+                        enqueue_unreferenced_delete(&conn, destination.as_ref(), &target_key).await
+                    {
+                        tracing::error!(error = %cleanup_error, storage_key = %target_key, "Failed to queue storage migration cleanup");
+                    }
                     return Err(error);
                 }
                 report.migrated += 1;