diff --git a/.github/workflows/desktop-windows-release-check.yaml b/.github/workflows/desktop-windows-release-check.yaml
index 2b81d2be4..6d8e933b9 100644
--- a/.github/workflows/desktop-windows-release-check.yaml
+++ b/.github/workflows/desktop-windows-release-check.yaml
@@ -23,6 +23,10 @@ on:
         required: false
         type: string
         default: ""
+      stale_apply_record:
+        description: Before each update, leave behind an hour-old record of an update that never installed (passes only when the installed versions retry it)
+        type: boolean
+        default: false
   pull_request:
     paths:
       - .github/workflows/desktop-windows-release-check.yaml
@@ -53,6 +57,7 @@ jobs:
       VERSION: ${{ inputs.version || '2026.1009.20411' }}
       EXPECT_FAILURE: ${{ github.event_name == 'pull_request' && 'true' || inputs.expect_failure }}
       UPDATE_FROM: ${{ inputs.update_from || '' }}
+      STALE_APPLY_RECORD: ${{ inputs.stale_apply_record && 'true' || 'false' }}
       ARCH: ${{ matrix.arch }}
     steps:
       - name: Checkout source
@@ -108,6 +113,13 @@ jobs:
             Get-Process | Where-Object { $_.Path -like "$installRoot*" } | Stop-Process -Force -ErrorAction SilentlyContinue
             $exe = Get-ChildItem -Path (Join-Path $installRoot 'current') -Filter 'Fluxer*.exe' | Where-Object { $_.Name -notlike '*_ExecutionStub.exe' } | Select-Object -First 1
             if ($null -eq $exe) { $failures += "$from did not install"; continue }
+            if ($env:STALE_APPLY_RECORD -eq 'true') {
+              $dataRoot = Split-Path (Split-Path $logPath -Parent) -Parent
+              New-Item -ItemType Directory -Force -Path $dataRoot | Out-Null
+              $attemptedAt = [DateTimeOffset]::UtcNow.AddHours(-1).ToUnixTimeMilliseconds()
+              Set-Content -Path (Join-Path $dataRoot 'update-apply-state.json') -Value "{`"version`":`"$env:VERSION`",`"attemptedAt`":$attemptedAt}" -NoNewline
+              Write-Host "left a stale apply record for $env:VERSION"
+            }
             Start-Process -FilePath $exe.FullName -ArgumentList '--disable-gpu'
             $deadline = (Get-Date).AddMinutes(8)
             $reported = $null
diff --git a/fluxer_desktop/src/main/ShellSelfUpdate.test.mjs b/fluxer_desktop/src/main/ShellSelfUpdate.test.mjs
index cf6260e85..8818fdbd5 100644
--- a/fluxer_desktop/src/main/ShellSelfUpdate.test.mjs
+++ b/fluxer_desktop/src/main/ShellSelfUpdate.test.mjs
@@ -342,7 +342,7 @@ describe('velopack self update', () => {
 	});
 
 	selfUpdateTest('an apply that never landed falls back instead of applying it again', async ({start}) => {
-		writeFileSync(applyStatePath, JSON.stringify({version: '2026.900.0', attemptedAt: 1}));
+		writeFileSync(applyStatePath, JSON.stringify({version: '2026.900.0', attemptedAt: Date.now() - 60_000}));
 		velopack.pendingRestart = {id: 'staged', Version: '2026.900.0'};
 		const {calls, hooks} = createHooks();
 
@@ -355,6 +355,24 @@ describe('velopack self update', () => {
 		assert.deepEqual(quits, []);
 	});
 
+	selfUpdateTest(
+		'an old apply that never landed retries from the feed instead of blocking every update',
+		async ({start, stillPending}) => {
+			writeFileSync(applyStatePath, JSON.stringify({version: '2026.900.0', attemptedAt: Date.now() - 3_600_000}));
+			velopack.pendingRestart = {id: 'staged', Version: '2026.900.0'};
+			velopack.checkResult = {id: 'v3', TargetFullRelease: {Version: '2026.950.0'}};
+			const {hooks} = createHooks();
+
+			assert.equal(await stillPending(start('velopack', hooks)), true);
+			assert.deepEqual(velopack.calls, [
+				'checkForUpdatesAsync',
+				'downloadUpdateAsync',
+				'waitExitThenApplyUpdate:v3:true:true',
+			]);
+			assert.equal(JSON.parse(readFileSync(applyStatePath, 'utf8')).version, '2026.950.0');
+		},
+	);
+
 	selfUpdateTest('an apply that landed is forgotten and the next one is recorded', async ({start, stillPending}) => {
 		writeFileSync(applyStatePath, JSON.stringify({version: '2026.800.0', attemptedAt: 1}));
 		velopack.pendingRestart = {id: 'staged', Version: '2026.900.0'};
diff --git a/fluxer_desktop/src/main/ShellSelfUpdate.ts b/fluxer_desktop/src/main/ShellSelfUpdate.ts
index 19679b13b..b4822fdae 100644
--- a/fluxer_desktop/src/main/ShellSelfUpdate.ts
+++ b/fluxer_desktop/src/main/ShellSelfUpdate.ts
@@ -73,14 +73,23 @@ function readInstalledVelopackVersion(manager: VelopackUpdateManager): string {
 	}
 }
 
-function hasUnlandedVelopackApply(manager: VelopackUpdateManager): boolean {
+const UNLANDED_APPLY_RETRY_AFTER_MS = 30 * 60_000;
+
+type UnlandedApply = 'none' | 'recent' | 'stale';
+
+function classifyUnlandedVelopackApply(manager: VelopackUpdateManager): UnlandedApply {
 	const attempt = readVelopackApplyAttempt();
-	if (attempt == null) return false;
+	if (attempt == null) return 'none';
 	if (compareShellVersions(readInstalledVelopackVersion(manager), attempt.version) >= 0) {
 		clearVelopackApplyAttempt();
-		return false;
+		return 'none';
 	}
-	return true;
+	if (Date.now() - attempt.attemptedAt < UNLANDED_APPLY_RETRY_AFTER_MS) {
+		return 'recent';
+	}
+	logger.warn('An earlier update never installed, retrying from the feed', {version: attempt.version});
+	clearVelopackApplyAttempt();
+	return 'stale';
 }
 
 function getStagedVelopackVersion(staged: UpdateInfo | VelopackAsset): string | null {
@@ -122,16 +131,19 @@ function downloadVelopackUpdateOnce(
 async function runVelopackSelfUpdate(control: SelfUpdateControl, hooks: ShellSelfUpdateHooks): Promise<void> {
 	const {UpdateManager} = requireModule('velopack') as typeof import('velopack');
 	const manager = new UpdateManager(getUpdateBaseUrl());
-	if (hasUnlandedVelopackApply(manager)) {
+	const unlanded = classifyUnlandedVelopackApply(manager);
+	if (unlanded === 'recent') {
 		control.settle({reason: 'install-failed', detail: 'the last downloaded update was never installed'});
 		return;
 	}
-	let staged: UpdateInfo | VelopackAsset | null;
-	try {
-		staged = manager.getUpdatePendingRestart();
-	} catch (error) {
-		control.settle({reason: 'check-failed', detail: errorDetail(error)});
-		return;
+	let staged: UpdateInfo | VelopackAsset | null = null;
+	if (unlanded === 'none') {
+		try {
+			staged = manager.getUpdatePendingRestart();
+		} catch (error) {
+			control.settle({reason: 'check-failed', detail: errorDetail(error)});
+			return;
+		}
 	}
 	if (control.isSettled()) return;
 	if (staged == null) {