diff --git a/.github/workflows/build.yml b/.github/workflows/build.yml
index fa01430..7df2e99 100644
--- a/.github/workflows/build.yml
+++ b/.github/workflows/build.yml
@@ -86,5 +86,7 @@ jobs:
         run: |
           rustup target add x86_64-apple-darwin
       - uses: tauri-apps/tauri-action@v0
+        env:
+          APPLE_SIGNING_IDENTITY: "-"
         with:
           args: ${{ matrix.args }}
diff --git a/.github/workflows/publish.yml b/.github/workflows/publish.yml
index a78fd6e..0feb71e 100644
--- a/.github/workflows/publish.yml
+++ b/.github/workflows/publish.yml
@@ -128,6 +128,7 @@ jobs:
       - uses: tauri-apps/tauri-action@v0
         env:
           GITHUB_TOKEN: ${{ secrets.GITHUB_TOKEN }}
+          APPLE_SIGNING_IDENTITY: "-"
         with:
           releaseId: ${{ needs.create-release.outputs.release_id }}
           args: ${{ matrix.args }}
diff --git a/src-tauri/src/lib.rs b/src-tauri/src/lib.rs
index 52a437e..31b02a8 100644
--- a/src-tauri/src/lib.rs
+++ b/src-tauri/src/lib.rs
@@ -12,6 +12,7 @@ struct AppState {
     uv_info: UvInfo,
     next_id: IdType,
     children: std::collections::HashMap<IdType, SpawnedProcessState>,
+    should_offer_tcc_reset: bool,
 }
 
 enum SpawnedProcessState {
@@ -458,6 +459,28 @@ fn kill_process_group(state: State<'_, Mutex<AppState>>, id: IdType) {
     // tracing::info!("Process group {id} has exited");
 }
 
+#[tauri::command]
+fn is_macos() -> bool {
+    cfg!(target_os = "macos")
+}
+
+#[tauri::command]
+fn get_should_offer_tcc_reset(state: State<'_, Mutex<AppState>>) -> bool {
+    state.lock().unwrap().should_offer_tcc_reset
+}
+
+#[tauri::command]
+fn run_tccutil_reset() -> Result<(), String> {
+    #[cfg(target_os = "macos")]
+    {
+        std::process::Command::new("/usr/bin/tccutil")
+            .args(["reset", "SystemPolicyAllFiles", "org.strawlab.Sunbeam"])
+            .output()
+            .map_err(|e| e.to_string())?;
+    }
+    Ok(())
+}
+
 /// Pick a free TCP port on localhost by binding to port 0 and reading back the
 /// assigned port. The listener is closed immediately, so there is a small race
 /// window before Jupyter binds the port, but this is acceptable in practice.
@@ -942,6 +965,24 @@ pub fn run() {
             // data, before we read or populate any defaults below.
             migrate_store(&store, &default_working_dir);
 
+            // On macOS, detect whether this is a new build since the last run.
+            // If so, the frontend will offer to reset TCC permissions, which
+            // can accumulate stale grants when an unsigned app is updated.
+            #[cfg(target_os = "macos")]
+            let should_offer_tcc_reset = {
+                let current_version = app.package_info().version.to_string();
+                let last_seen = store
+                    .get("lastKnownBuildVersion")
+                    .and_then(|v| v.as_str().map(str::to_owned));
+                // Only offer on genuine updates — suppress on first install
+                // (no prior grants exist yet, so nothing useful to reset).
+                let offer = matches!(&last_seen, Some(v) if v != &current_version);
+                store.set("lastKnownBuildVersion", serde_json::json!(current_version));
+                offer
+            };
+            #[cfg(not(target_os = "macos"))]
+            let should_offer_tcc_reset = false;
+
             // // Note that values must be serde_json::Value instances,
             // // otherwise, they will not be compatible with the JavaScript bindings.
             // store.set("some-key", json!({ "value": 5 }));
@@ -960,6 +1001,7 @@ pub fn run() {
                 uv_info,
                 next_id: Default::default(),
                 children: Default::default(),
+                should_offer_tcc_reset,
             }));
             Ok(())
         })
@@ -975,7 +1017,10 @@ pub fn run() {
             parse_pyproject_toml,
             process_group_state,
             kill_process_group,
-            spawn_uv
+            spawn_uv,
+            is_macos,
+            get_should_offer_tcc_reset,
+            run_tccutil_reset,
         ])
         .build(tauri::generate_context!())
         .expect("error while building tauri application");
diff --git a/src/App.tsx b/src/App.tsx
index 662df76..69b3b6f 100644
--- a/src/App.tsx
+++ b/src/App.tsx
@@ -3,7 +3,7 @@ import { Sun, Package, Play, FolderOpen, Check, Copy, Loader2, ChevronDown, Chev
 
 import { invoke, Channel } from "@tauri-apps/api/core";
 import "./App.css";
-import { open } from '@tauri-apps/plugin-dialog';
+import { open, ask } from '@tauri-apps/plugin-dialog';
 import { openUrl } from '@tauri-apps/plugin-opener';
 
 type SpawnedProcessEvent = {
@@ -526,6 +526,7 @@ function App() {
   const [configLoaded, setConfigLoaded] = useState(false);
 
   const [workingDir, setWorkingDir] = useState("");
+  const [isMacos, setIsMacos] = useState(false);
 
   // Custom package input state
   const [customPackageName, setCustomPackageName] = useState("");
@@ -544,11 +545,13 @@ function App() {
   const [uploadMessage, setUploadMessage] = useState<string>('');
 
   useEffect(() => {
-    // Load initial configuration
+    // Load initial configuration and check for macOS TCC reset offer
     Promise.all([
       invoke<string>("get_cwd"),
-      invoke<PackageConfig>("get_package_config")
-    ]).then(([cwd, config]) => {
+      invoke<PackageConfig>("get_package_config"),
+      invoke<boolean>("is_macos"),
+      invoke<boolean>("get_should_offer_tcc_reset"),
+    ]).then(async ([cwd, config, macos, shouldReset]) => {
       setWorkingDir(cwd);
       setPythonVersion(config.pythonVersion);
 
@@ -566,6 +569,21 @@ function App() {
 
       setPackages(packageMap);
       setConfigLoaded(true);
+      setIsMacos(macos);
+
+      if (shouldReset) {
+        const confirmed = await ask(
+          "Sunbeam has been updated. Due to a known macOS behavior with unsigned apps, " +
+          "file permissions from the previous version may not carry over correctly, " +
+          "which can cause repeated permission prompts.\n\n" +
+          "Would you like Sunbeam to reset its file access now? macOS will ask you " +
+          "to re-grant access the next time it's needed.",
+          { title: "Reset file permissions?", okLabel: "Reset Now", cancelLabel: "Not Now" }
+        );
+        if (confirmed) {
+          await invoke("run_tccutil_reset");
+        }
+      }
     });
   }, []);
 
@@ -684,6 +702,16 @@ function App() {
     });
   };
 
+  const handleManualTccReset = async () => {
+    const confirmed = await ask(
+      "This will reset Sunbeam's file access permissions. macOS will ask you to re-grant access the next time it's needed.",
+      { title: "Reset file permissions?", okLabel: "Reset Now", cancelLabel: "Cancel" }
+    );
+    if (confirmed) {
+      await invoke("run_tccutil_reset");
+    }
+  };
+
   const selectWorkingDir = async () => {
 
     const dirHandle = await open({
@@ -1065,6 +1093,20 @@ function App() {
               Launch Jupyter Lab
             </button>
           </div>
+
+          {/* macOS file permission reset — only shown on macOS */}
+          {isMacos && (
+            <div className="mt-4 pt-4 border-t border-gray-100 flex items-center justify-between">
+              <p className="text-xs text-gray-400">Having repeated permission prompts?</p>
+              <button
+                onClick={handleManualTccReset}
+                className="text-xs text-gray-400 hover:text-amber-600 underline transition"
+                title="Reset Sunbeam's macOS file access permissions (Documents, Downloads)"
+              >
+                Reset macOS file permissions
+              </button>
+            </div>
+          )}
         </div>
       </div>