diff --git a/scripts/desktop-tauri-build.mjs b/scripts/desktop-tauri-build.mjs
index c2196f9d78..fcf1ae263e 100644
--- a/scripts/desktop-tauri-build.mjs
+++ b/scripts/desktop-tauri-build.mjs
@@ -71,14 +71,23 @@ async function main() {
   });
   const tauriBin = join(ROOT, 'node_modules', '.bin', 'tauri');
   const tauriArgs = ['build', '--config', tauriConfig, ...forward];
-  const buildStartedAtMs = Date.now();
+  let attemptStartedAtMs = Date.now();
   let r = runTauriBuild(tauriBin, tauriArgs, desktopDir);
 
-  if (!r.error && shouldRetryMacDmgBuild(r, forward, desktopDir, buildStartedAtMs)) {
+  const maxMacDmgBuildAttempts = 3;
+  for (
+    let attempt = 1;
+    attempt < maxMacDmgBuildAttempts
+      && !r.error
+      && shouldRetryMacDmgBuild(r, forward, desktopDir, attemptStartedAtMs);
+    attempt += 1
+  ) {
+    const retryDelaySeconds = attempt * 10;
     console.warn(
-      '[tauri-build] DMG bundling failed after the macOS app bundle was created; retrying once in 10 seconds.'
+      `[tauri-build] DMG bundling failed after the macOS app bundle was refreshed; retrying build attempt ${attempt + 1}/${maxMacDmgBuildAttempts} in ${retryDelaySeconds} seconds.`
     );
-    await new Promise((resolveRetry) => setTimeout(resolveRetry, 10_000));
+    await new Promise((resolveRetry) => setTimeout(resolveRetry, retryDelaySeconds * 1_000));
+    attemptStartedAtMs = Date.now();
     r = runTauriBuild(tauriBin, tauriArgs, desktopDir);
   }
 
@@ -169,13 +178,28 @@ export function shouldRetryMacDmgBuild(
     'macos'
   );
 
+  const freshAfterMs = buildStartedAtMs - 1_000;
   try {
-    return readdirSync(bundleDir, { withFileTypes: true }).some(
-      (entry) =>
-        entry.isDirectory() &&
-        entry.name.endsWith('.app') &&
-        statSync(join(bundleDir, entry.name)).mtimeMs >= buildStartedAtMs - 1_000
-    );
+    return readdirSync(bundleDir, { withFileTypes: true }).some((entry) => {
+      if (!entry.isDirectory() || !entry.name.endsWith('.app')) {
+        return false;
+      }
+
+      const appDir = join(bundleDir, entry.name);
+      if (statSync(appDir).mtimeMs >= freshAfterMs) {
+        return true;
+      }
+
+      // The Rust cache can restore an existing app directory without changing
+      // its own mtime. Tauri still refreshes the executable inside it before
+      // codesigning, so use that file as the reliable bundling boundary.
+      const executableDir = join(appDir, 'Contents', 'MacOS');
+      return readdirSync(executableDir, { withFileTypes: true }).some(
+        (executable) =>
+          executable.isFile()
+          && statSync(join(executableDir, executable.name)).mtimeMs >= freshAfterMs
+      );
+    });
   } catch {
     return false;
   }
diff --git a/scripts/desktop-tauri-build.test.mjs b/scripts/desktop-tauri-build.test.mjs
index 0826f10e22..40037fa28d 100644
--- a/scripts/desktop-tauri-build.test.mjs
+++ b/scripts/desktop-tauri-build.test.mjs
@@ -170,12 +170,16 @@ function retryFixture() {
     'macos',
     'OpenBitFun.app'
   );
+  const executableDir = join(appDir, 'Contents', 'MacOS');
+  const executablePath = join(executableDir, 'openbitfun-desktop');
   mkdirSync(desktopDir, { recursive: true });
-  mkdirSync(appDir, { recursive: true });
+  mkdirSync(executableDir, { recursive: true });
+  writeFileSync(executablePath, 'test executable');
 
   return {
     appDir,
     desktopDir,
+    executablePath,
     runtime: {
       cargoTargetDir: targetDir,
       githubActions: 'true',
@@ -204,6 +208,28 @@ test('retries a failed GitHub Actions DMG bundle after a fresh app bundle', () =
   }
 });
 
+test('retries when a restored app directory contains a freshly bundled executable', () => {
+  const fixture = retryFixture();
+  try {
+    const buildStartedAt = Date.now();
+    const staleTime = new Date(buildStartedAt - 60_000);
+    utimesSync(fixture.appDir, staleTime, staleTime);
+
+    assert.equal(
+      shouldRetryMacDmgBuild(
+        FAILED_BUILD,
+        DMG_ARGS,
+        fixture.desktopDir,
+        buildStartedAt,
+        fixture.runtime
+      ),
+      true
+    );
+  } finally {
+    fixture.cleanup();
+  }
+});
+
 test('does not retry failures outside the narrow DMG bundling boundary', () => {
   const fixture = retryFixture();
   try {
@@ -228,6 +254,7 @@ test('does not retry failures outside the narrow DMG bundling boundary', () => {
 
     const staleTime = new Date(Date.now() - 60_000);
     utimesSync(fixture.appDir, staleTime, staleTime);
+    utimesSync(fixture.executablePath, staleTime, staleTime);
     assert.equal(
       shouldRetryMacDmgBuild(
         FAILED_BUILD,