From 6cd56beada52dcc3009ca8b36b6a30b6340182ef Mon Sep 17 00:00:00 2001
From: John Trujillo <johnandrestrujillo@gmail.com>
Date: Mon, 20 Jul 2026 16:10:04 -0500
Subject: [PATCH 1/2] fix(ai-assistant): resolve file picker crashes and secure
 API key

- Fix file picker empty state and `BadTokenException` by using the correct project context (`IdeProjectService`) and moving I/O off the main thread.
- Secure Gemini API key with hardware-backed Keystore encryption (including legacy migration) and add a show/hide toggle.
- Improve UI by replacing emoji markers with vector drawables and extracting hardcoded strings to `strings.xml`.
---
 .../fragments/AiSettingsFragment.kt           |  65 ++++-
 .../aiassistant/fragments/ChatFragment.kt     |  13 +-
 .../fragments/FilePickerDialogFragment.kt     | 267 ++++++++++++------
 .../aiassistant/security/SecureApiKeyStore.kt | 114 ++++++++
 .../viewmodel/AiSettingsViewModel.kt          |  27 +-
 .../src/main/res/drawable/ic_check.xml        |  10 +
 .../src/main/res/drawable/ic_file.xml         |  10 +
 .../src/main/res/drawable/ic_folder.xml       |  10 +
 .../src/main/res/drawable/ic_visibility.xml   |  10 +
 .../main/res/drawable/ic_visibility_off.xml   |  10 +
 .../src/main/res/layout/item_file_picker.xml  |  34 +++
 .../res/layout/layout_settings_gemini_api.xml |  30 +-
 ai-assistant/src/main/res/values/strings.xml  |  16 ++
 .../plugins/aicore/GeminiBackend.kt           |   5 +-
 .../plugins/aicore/SecureApiKeyStore.kt       | 114 ++++++++
 15 files changed, 615 insertions(+), 120 deletions(-)
 create mode 100644 ai-assistant/src/main/kotlin/com/itsaky/androidide/plugins/aiassistant/security/SecureApiKeyStore.kt
 create mode 100644 ai-assistant/src/main/res/drawable/ic_check.xml
 create mode 100644 ai-assistant/src/main/res/drawable/ic_file.xml
 create mode 100644 ai-assistant/src/main/res/drawable/ic_folder.xml
 create mode 100644 ai-assistant/src/main/res/drawable/ic_visibility.xml
 create mode 100644 ai-assistant/src/main/res/drawable/ic_visibility_off.xml
 create mode 100644 ai-assistant/src/main/res/layout/item_file_picker.xml
 create mode 100644 ai-core/src/main/kotlin/com/itsaky/androidide/plugins/aicore/SecureApiKeyStore.kt

diff --git a/ai-assistant/src/main/kotlin/com/itsaky/androidide/plugins/aiassistant/fragments/AiSettingsFragment.kt b/ai-assistant/src/main/kotlin/com/itsaky/androidide/plugins/aiassistant/fragments/AiSettingsFragment.kt
index 83c285c1..8c0686a4 100644
--- a/ai-assistant/src/main/kotlin/com/itsaky/androidide/plugins/aiassistant/fragments/AiSettingsFragment.kt
+++ b/ai-assistant/src/main/kotlin/com/itsaky/androidide/plugins/aiassistant/fragments/AiSettingsFragment.kt
@@ -5,6 +5,8 @@ import android.content.Context
 import android.content.Intent
 import android.net.Uri
 import android.os.Bundle
+import android.text.method.HideReturnsTransformationMethod
+import android.text.method.PasswordTransformationMethod
 import android.view.LayoutInflater
 import android.view.View
 import android.view.ViewGroup
@@ -290,6 +292,7 @@ class AiSettingsFragment : DialogFragment() {
     private fun setupGeminiApiUi(view: View) {
         val apiKeyLayout = view.findViewById<LinearLayout>(R.id.gemini_api_key_layout)
         val apiKeyInput = view.findViewById<EditText>(R.id.gemini_api_key_input)
+        val toggleVisibilityButton = view.findViewById<ImageButton>(R.id.btn_toggle_api_key_visibility)
         val saveButton = view.findViewById<Button>(R.id.btn_save_api_key)
         val editButton = view.findViewById<Button>(R.id.btn_edit_api_key)
         val clearButton = view.findViewById<Button>(R.id.btn_clear_api_key)
@@ -328,37 +331,69 @@ class AiSettingsFragment : DialogFragment() {
             if (timestamp > 0) {
                 val sdf = SimpleDateFormat("MMMM d, yyyy", Locale.getDefault())
                 val savedDate = sdf.format(Date(timestamp))
-                statusTextView.text = "API Key saved on: $savedDate"
+                statusTextView.text = getString(R.string.msg_api_key_saved_on, savedDate)
             } else {
-                statusTextView.text = "API Key is saved"
+                statusTextView.text = getString(R.string.msg_api_key_is_saved)
             }
         }
 
-        saveButton.setOnClickListener {
-            val apiKey = apiKeyInput.text.toString()
-            if (apiKey.isNotBlank()) {
-                viewModel.saveGeminiApiKey(apiKey)
-                Toast.makeText(requireContext(), "API Key saved", Toast.LENGTH_SHORT).show()
+        toggleVisibilityButton.setColorFilter(apiKeyInput.currentHintTextColor)
 
-                updateUiState(isEditing = false)
-                val timestamp = viewModel.getGeminiApiKeySaveTimestamp()
-                val sdf = SimpleDateFormat("MMMM d, yyyy", Locale.getDefault())
-                val savedDate = sdf.format(Date(timestamp))
-                statusTextView.text = "API Key saved on: $savedDate"
+        var isKeyVisible = false
+
+        fun applyKeyVisibility() {
+            apiKeyInput.transformationMethod = if (isKeyVisible) {
+                HideReturnsTransformationMethod.getInstance()
             } else {
-                Toast.makeText(requireContext(), "API Key cannot be empty", Toast.LENGTH_SHORT).show()
+                PasswordTransformationMethod.getInstance()
             }
+            toggleVisibilityButton.setImageResource(
+                if (isKeyVisible) R.drawable.ic_visibility_off else R.drawable.ic_visibility
+            )
+            toggleVisibilityButton.contentDescription = getString(
+                if (isKeyVisible) R.string.cd_hide_api_key else R.string.cd_show_api_key
+            )
+            toggleVisibilityButton.setColorFilter(apiKeyInput.currentHintTextColor)
+            apiKeyInput.setSelection(apiKeyInput.text?.length ?: 0)
+        }
+
+        applyKeyVisibility()
+
+        toggleVisibilityButton.setOnClickListener {
+            isKeyVisible = !isKeyVisible
+            applyKeyVisibility()
+        }
+
+        saveButton.setOnClickListener {
+            val apiKey = apiKeyInput.text.toString().trim()
+            if (apiKey.isBlank()) {
+                Toast.makeText(requireContext(), getString(R.string.msg_api_key_empty), Toast.LENGTH_SHORT).show()
+                return@setOnClickListener
+            }
+            if (!viewModel.saveGeminiApiKey(apiKey)) {
+                Toast.makeText(requireContext(), getString(R.string.msg_api_key_save_failed), Toast.LENGTH_LONG).show()
+                return@setOnClickListener
+            }
+            Toast.makeText(requireContext(), getString(R.string.msg_api_key_saved), Toast.LENGTH_SHORT).show()
+
+            updateUiState(isEditing = false)
+            val timestamp = viewModel.getGeminiApiKeySaveTimestamp()
+            val sdf = SimpleDateFormat("MMMM d, yyyy", Locale.getDefault())
+            val savedDate = sdf.format(Date(timestamp))
+            statusTextView.text = getString(R.string.msg_api_key_saved_on, savedDate)
         }
 
         editButton.setOnClickListener {
             updateUiState(isEditing = true)
-            apiKeyInput.setText("••••••••••••••••")
+            apiKeyInput.setText(viewModel.getGeminiApiKey().orEmpty())
+            isKeyVisible = false
+            applyKeyVisibility()
             apiKeyInput.requestFocus()
         }
 
         clearButton.setOnClickListener {
             viewModel.clearGeminiApiKey()
-            Toast.makeText(requireContext(), "API Key cleared", Toast.LENGTH_SHORT).show()
+            Toast.makeText(requireContext(), getString(R.string.msg_api_key_cleared), Toast.LENGTH_SHORT).show()
             updateUiState(isEditing = true)
             apiKeyInput.setText("")
         }
diff --git a/ai-assistant/src/main/kotlin/com/itsaky/androidide/plugins/aiassistant/fragments/ChatFragment.kt b/ai-assistant/src/main/kotlin/com/itsaky/androidide/plugins/aiassistant/fragments/ChatFragment.kt
index a293646f..881c8a69 100644
--- a/ai-assistant/src/main/kotlin/com/itsaky/androidide/plugins/aiassistant/fragments/ChatFragment.kt
+++ b/ai-assistant/src/main/kotlin/com/itsaky/androidide/plugins/aiassistant/fragments/ChatFragment.kt
@@ -15,9 +15,11 @@ import androidx.recyclerview.widget.LinearLayoutManager
 import com.google.android.material.chip.Chip
 import com.itsaky.androidide.plugins.PluginContext
 import com.itsaky.androidide.plugins.aiassistant.adapters.ChatAdapter
+import com.itsaky.androidide.plugins.aiassistant.tool.handlers.PathGuard
 import com.itsaky.androidide.plugins.aiassistant.databinding.FragmentChatBinding
 import com.itsaky.androidide.plugins.aiassistant.models.AgentState
 import com.itsaky.androidide.plugins.aiassistant.viewmodel.ChatViewModel
+import com.itsaky.androidide.plugins.services.IdeProjectService
 import io.noties.markwon.Markwon
 import kotlinx.coroutines.launch
 import java.io.File
@@ -334,9 +336,16 @@ class ChatFragment : Fragment() {
         dialog.show(parentFragmentManager, "approval_dialog")
     }
 
+    /**
+     * Opens the file picker rooted at the open project. The host's
+     * [IdeProjectService] is the source of truth for the project root; the
+     * `System.getProperty` chain in [PathGuard] resolves to "/" at runtime (the
+     * IDE process cwd), which lists nothing, so it is only a last-resort fallback.
+     */
     private fun showFilePicker() {
-        // Start from AndroidIDE projects directory by default
-        val startPath = "/storage/emulated/0/AndroidIDEProjects"
+        val projectService = getPluginContext()?.services?.get(IdeProjectService::class.java)
+        val startPath = projectService?.getCurrentProject()?.rootDir?.absolutePath
+            ?: PathGuard.projectRoot()
 
         val dialog = FilePickerDialogFragment.newInstance(startPath) { files ->
             addContextFiles(files)
diff --git a/ai-assistant/src/main/kotlin/com/itsaky/androidide/plugins/aiassistant/fragments/FilePickerDialogFragment.kt b/ai-assistant/src/main/kotlin/com/itsaky/androidide/plugins/aiassistant/fragments/FilePickerDialogFragment.kt
index bc7e2dfa..cba1cfbb 100644
--- a/ai-assistant/src/main/kotlin/com/itsaky/androidide/plugins/aiassistant/fragments/FilePickerDialogFragment.kt
+++ b/ai-assistant/src/main/kotlin/com/itsaky/androidide/plugins/aiassistant/fragments/FilePickerDialogFragment.kt
@@ -1,143 +1,232 @@
 package com.itsaky.androidide.plugins.aiassistant.fragments
 
 import android.app.Dialog
+import android.content.Context
 import android.os.Bundle
+import android.view.LayoutInflater
+import android.view.View
+import android.view.ViewGroup
 import android.widget.ArrayAdapter
+import android.widget.ImageView
 import android.widget.ListView
+import android.widget.TextView
+import androidx.appcompat.app.AlertDialog
+import androidx.appcompat.view.ContextThemeWrapper
+import androidx.core.view.isVisible
 import androidx.fragment.app.DialogFragment
+import androidx.lifecycle.lifecycleScope
 import com.google.android.material.dialog.MaterialAlertDialogBuilder
+import com.itsaky.androidide.plugins.aiassistant.R
+import com.itsaky.androidide.plugins.aiassistant.tool.handlers.PathGuard
+import kotlinx.coroutines.Dispatchers
+import kotlinx.coroutines.launch
+import kotlinx.coroutines.withContext
 import java.io.File
 
 /**
- * Dialog for picking files to add as context.
+ * Dialog for picking project files to add as chat context.
+ *
+ * The dialog is created once and refreshed **in place** as the user navigates
+ * or toggles selection. It never dismisses-and-recreates itself: doing so
+ * detaches the fragment from its context, after which a follow-up
+ * `requireContext()` throws `IllegalStateException: not attached to a context`
+ * (previously crashed on the second "Toggle All").
+ *
+ * Navigation is confined to the start path supplied by the caller (the open
+ * project root), so the picker can't be used to reach arbitrary files on the
+ * device. All disk I/O runs off the main thread; see [computeListing].
  */
 class FilePickerDialogFragment : DialogFragment() {
 
     private var onFilesSelected: ((List<File>) -> Unit)? = null
-    private var currentDirectory: File? = null
     private val selectedFiles = mutableSetOf<File>()
 
+    /** Root the picker is confined to; navigation can never go above this. */
+    private lateinit var rootDirectory: File
+    private lateinit var currentDirectory: File
+
+    // Reused across in-place refreshes so we never rebuild the Dialog/Fragment.
+    private val rows = mutableListOf<FileRow>()
+    private lateinit var listAdapter: FileRowAdapter
+    private var alertDialog: AlertDialog? = null
+
     companion object {
         private const val ARG_START_PATH = "start_path"
+        private const val PARENT_NAME = ".."
 
         fun newInstance(
             startPath: String? = null,
             onSelected: (List<File>) -> Unit
         ): FilePickerDialogFragment {
             return FilePickerDialogFragment().apply {
+                // Default to the current project root when no path is given.
                 arguments = Bundle().apply {
-                    // Use provided path or default to storage root
-                    val path = startPath ?: "/storage/emulated/0"
-                    putString(ARG_START_PATH, path)
+                    putString(ARG_START_PATH, startPath ?: PathGuard.projectRoot())
                 }
                 onFilesSelected = onSelected
             }
         }
     }
 
-    override fun onCreateDialog(savedInstanceState: Bundle?): Dialog {
-        val startPath = arguments?.getString(ARG_START_PATH) ?: "/storage/emulated/0"
-        currentDirectory = File(startPath)
+    /** One navigable entry: a directory to descend into or a selectable file. */
+    private data class FileRow(
+        val file: File,
+        val displayName: String,
+        val isDirectory: Boolean,
+    )
 
-        if (!currentDirectory!!.exists()) {
-            // Fallback to root if start path doesn't exist
-            currentDirectory = File("/storage/emulated/0")
+    /** Result of a directory scan, computed off the main thread. */
+    private data class Listing(val rows: List<FileRow>, val directory: File)
+
+    override fun onCreateDialog(savedInstanceState: Bundle?): Dialog {
+        val context = ContextThemeWrapper(requireContext(), R.style.PluginTheme)
+        listAdapter = FileRowAdapter(context)
+        val listView = ListView(context).apply {
+            adapter = listAdapter
+            setOnItemClickListener { _, _, position, _ -> onItemClicked(position) }
         }
 
-        if (!currentDirectory!!.exists()) {
-            return MaterialAlertDialogBuilder(requireContext())
-                .setTitle("Error")
-                .setMessage("Storage directory not found")
-                .setPositiveButton("OK") { _, _ -> dismiss() }
-                .create()
+        val dialog = MaterialAlertDialogBuilder(context)
+            .setTitle(R.string.file_picker_title)
+            .setView(listView)
+            .setPositiveButton(R.string.file_picker_add_selected) { _, _ ->
+                onFilesSelected?.invoke(selectedFiles.toList())
+            }
+            .setNegativeButton(android.R.string.cancel, null)
+            // Wired in setOnShowListener so the click doesn't auto-dismiss the dialog.
+            .setNeutralButton(R.string.file_picker_toggle_all, null)
+            .create()
+
+        dialog.setOnShowListener {
+            dialog.getButton(AlertDialog.BUTTON_NEUTRAL)?.setOnClickListener {
+                toggleAllInCurrentDirectory()
+            }
         }
+        alertDialog = dialog
+        loadInitial()
+        return dialog
+    }
 
-        return showDirectoryPicker(currentDirectory!!)
+    /**
+     * Resolve the confined root from the start path and load its listing.
+     * The start path passed by the caller IS the confinement root — the picker
+     * confines navigation to the open project and starts there.
+     */
+    private fun loadInitial() {
+        val rootPath = arguments?.getString(ARG_START_PATH) ?: PathGuard.projectRoot()
+        lifecycleScope.launch {
+            val listing = withContext(Dispatchers.IO) {
+                rootDirectory = File(rootPath).canonicalOrAbsolute()
+                if (!rootDirectory.exists()) {
+                    null
+                } else {
+                    currentDirectory = rootDirectory
+                    computeListing(rootDirectory)
+                }
+            }
+            if (listing == null) {
+                alertDialog?.setTitle(getString(R.string.file_picker_error_not_found))
+            } else {
+                applyListing(listing)
+            }
+        }
     }
 
-    private fun showDirectoryPicker(directory: File): Dialog {
-        val files = directory.listFiles()?.sortedWith(
-            compareBy<File> { !it.isDirectory }
-                .thenBy { it.name }
-        ) ?: emptyList()
+    /** Recompute the listing for [directory] off-thread and apply it in place. */
+    private fun populate(directory: File) {
+        lifecycleScope.launch {
+            val listing = withContext(Dispatchers.IO) {
+                currentDirectory = directory
+                computeListing(directory)
+            }
+            applyListing(listing)
+        }
+    }
 
-        val items = mutableListOf<String>()
-        val fileList = mutableListOf<File>()
+    /** Pure disk I/O — must run on a background dispatcher. */
+    private fun computeListing(directory: File): Listing {
+        val newRows = mutableListOf<FileRow>()
 
-        // Add parent directory option if not at root
-        if (directory.parentFile != null && directory.parentFile!!.exists()) {
-            items.add("📁 ..")
-            fileList.add(directory.parentFile!!)
+        // Offer ".." only while the parent is still inside the confined root.
+        val parent = directory.parentFile
+        if (parent != null && parent.exists() && isWithinRoot(parent) &&
+            canonical(directory) != canonical(rootDirectory)
+        ) {
+            newRows.add(FileRow(parent, PARENT_NAME, isDirectory = true))
         }
 
-        // Add directories and files
-        files.forEach { file ->
-            val prefix = if (file.isDirectory) "📁 " else "📄 "
-            val suffix = if (selectedFiles.contains(file)) " ✓" else ""
-            items.add("$prefix${file.name}$suffix")
-            fileList.add(file)
-        }
+        directory.listFiles()
+            ?.sortedWith(compareBy<File> { !it.isDirectory }.thenBy { it.name.lowercase() })
+            ?.forEach { file -> newRows.add(FileRow(file, file.name, file.isDirectory)) }
+
+        return Listing(newRows, directory)
+    }
 
-        val adapter = ArrayAdapter(
-            requireContext(),
-            android.R.layout.simple_list_item_1,
-            items
-        )
+    /** Swap in a freshly computed [listing] — main thread only. */
+    private fun applyListing(listing: Listing) {
+        rows.clear()
+        rows.addAll(listing.rows)
+        listAdapter.notifyDataSetChanged()
+        alertDialog?.setTitle(titleFor(listing.directory))
+    }
 
-        val listView = ListView(requireContext()).apply {
-            this.adapter = adapter
-            choiceMode = ListView.CHOICE_MODE_MULTIPLE
+    private fun onItemClicked(position: Int) {
+        val row = rows[position]
+        if (row.isDirectory) {
+            populate(row.file)
+        } else {
+            if (!selectedFiles.remove(row.file)) selectedFiles.add(row.file)
+            listAdapter.notifyDataSetChanged()
         }
+    }
 
-        return MaterialAlertDialogBuilder(requireContext())
-            .setTitle("Select Files: ${directory.name}")
-            .setView(listView)
-            .setPositiveButton("Add Selected") { _, _ ->
-                onFilesSelected?.invoke(selectedFiles.toList())
-                dismiss()
-            }
-            .setNegativeButton("Cancel") { _, _ -> dismiss() }
-            .setNeutralButton("Toggle All") { _, _ ->
-                // Toggle all files in current directory
-                val currentFiles = files.filter { it.isFile }
-                if (selectedFiles.containsAll(currentFiles)) {
-                    selectedFiles.removeAll(currentFiles.toSet())
-                } else {
-                    selectedFiles.addAll(currentFiles)
-                }
-                // Refresh dialog
-                dismiss()
-                showDirectoryPicker(directory).show()
-            }
-            .create().apply {
-                listView.setOnItemClickListener { _, _, position, _ ->
-                    val file = fileList[position]
-
-                    if (file.isDirectory) {
-                        // Navigate to directory
-                        dismiss()
-                        showDirectoryPicker(file).show()
-                    } else {
-                        // Toggle file selection
-                        if (selectedFiles.contains(file)) {
-                            selectedFiles.remove(file)
-                        } else {
-                            selectedFiles.add(file)
-                        }
-                        // Refresh display
-                        items[position] = if (selectedFiles.contains(file)) {
-                            "📄 ${file.name} ✓"
-                        } else {
-                            "📄 ${file.name}"
-                        }
-                        adapter.notifyDataSetChanged()
-                    }
-                }
-            }
+    private fun toggleAllInCurrentDirectory() {
+        val currentFiles = rows.filter { !it.isDirectory }.map { it.file }
+        if (currentFiles.isEmpty()) return
+        if (selectedFiles.containsAll(currentFiles)) {
+            selectedFiles.removeAll(currentFiles.toSet())
+        } else {
+            selectedFiles.addAll(currentFiles)
+        }
+        listAdapter.notifyDataSetChanged()
+    }
+
+    private fun titleFor(dir: File): String =
+        getString(R.string.file_picker_title_current, dir.name)
+
+    private fun isWithinRoot(dir: File): Boolean {
+        val root = canonical(rootDirectory)
+        val path = canonical(dir)
+        return path == root || path.startsWith(root + File.separator)
     }
 
+    private fun canonical(f: File): String =
+        try { f.canonicalPath } catch (e: Exception) { f.absolutePath }
+
+    private fun File.canonicalOrAbsolute(): File =
+        try { canonicalFile } catch (e: Exception) { absoluteFile }
+
     override fun onDestroyView() {
         super.onDestroyView()
         onFilesSelected = null
+        alertDialog = null
+    }
+
+    /** Binds each [FileRow] to [R.layout.item_file_picker]; the check reflects selection. */
+    private inner class FileRowAdapter(context: Context) :
+        ArrayAdapter<FileRow>(context, 0, rows) {
+
+        override fun getView(position: Int, convertView: View?, parent: ViewGroup): View {
+            val view = convertView
+                ?: LayoutInflater.from(parent.context).inflate(R.layout.item_file_picker, parent, false)
+            val row = getItem(position) ?: return view
+
+            view.findViewById<ImageView>(R.id.file_picker_row_icon)
+                .setImageResource(if (row.isDirectory) R.drawable.ic_folder else R.drawable.ic_file)
+            view.findViewById<TextView>(R.id.file_picker_row_name).text = row.displayName
+            view.findViewById<ImageView>(R.id.file_picker_row_check).isVisible =
+                selectedFiles.contains(row.file)
+            return view
+        }
     }
 }
diff --git a/ai-assistant/src/main/kotlin/com/itsaky/androidide/plugins/aiassistant/security/SecureApiKeyStore.kt b/ai-assistant/src/main/kotlin/com/itsaky/androidide/plugins/aiassistant/security/SecureApiKeyStore.kt
new file mode 100644
index 00000000..fe42be23
--- /dev/null
+++ b/ai-assistant/src/main/kotlin/com/itsaky/androidide/plugins/aiassistant/security/SecureApiKeyStore.kt
@@ -0,0 +1,114 @@
+package com.itsaky.androidide.plugins.aiassistant.security
+
+import android.security.keystore.KeyGenParameterSpec
+import android.security.keystore.KeyPermanentlyInvalidatedException
+import android.security.keystore.KeyProperties
+import android.util.Base64
+import android.util.Log
+import java.security.GeneralSecurityException
+import java.security.KeyStore
+import javax.crypto.Cipher
+import javax.crypto.KeyGenerator
+import javax.crypto.SecretKey
+import javax.crypto.spec.GCMParameterSpec
+
+/**
+ * AES/GCM encryption for sensitive settings (currently the Gemini API key),
+ * keyed by a hardware-backed Android Keystore secret. Only ciphertext is
+ * written to SharedPreferences, so a copied prefs file (root, `adb backup`,
+ * forensic dump) is useless without this device's Keystore.
+ *
+ * The alias and transform below are mirrored verbatim in ai-core's
+ * `SecureApiKeyStore` so a key written here can be decrypted there — both
+ * plugins run in the host app's process (same UID) and therefore share one
+ * Android Keystore. Keep the two copies in sync.
+ */
+object SecureApiKeyStore {
+    private const val TAG = "SecureApiKeyStore"
+    private const val KEYSTORE = "AndroidKeyStore"
+    private const val ALIAS = "cotg_ai_gemini_key_v1"
+    private const val TRANSFORM = "AES/GCM/NoPadding"
+    private const val IV_LEN = 12
+    private const val TAG_BITS = 128
+
+    /** Marks a stored value as ciphertext; anything without it is treated as legacy plaintext. */
+    const val ENC_PREFIX = "enc:v1:"
+
+    private fun getOrCreateKey(): SecretKey {
+        val ks = KeyStore.getInstance(KEYSTORE).apply { load(null) }
+        (ks.getEntry(ALIAS, null) as? KeyStore.SecretKeyEntry)?.let { return it.secretKey }
+        val generator = KeyGenerator.getInstance(KeyProperties.KEY_ALGORITHM_AES, KEYSTORE)
+        generator.init(
+            KeyGenParameterSpec.Builder(
+                ALIAS,
+                KeyProperties.PURPOSE_ENCRYPT or KeyProperties.PURPOSE_DECRYPT
+            )
+                .setBlockModes(KeyProperties.BLOCK_MODE_GCM)
+                .setEncryptionPaddings(KeyProperties.ENCRYPTION_PADDING_NONE)
+                .build()
+        )
+        return generator.generateKey()
+    }
+
+    private fun deleteKey() {
+        try {
+            KeyStore.getInstance(KEYSTORE).apply { load(null) }.deleteEntry(ALIAS)
+        } catch (e: Exception) {
+            Log.w(TAG, "Failed to delete Keystore alias $ALIAS", e)
+        }
+    }
+
+    private fun encryptWith(key: SecretKey, plain: String): String {
+        val cipher = Cipher.getInstance(TRANSFORM)
+        cipher.init(Cipher.ENCRYPT_MODE, key)
+        val iv = cipher.iv
+        val ciphertext = cipher.doFinal(plain.toByteArray(Charsets.UTF_8))
+        val combined = ByteArray(iv.size + ciphertext.size)
+        System.arraycopy(iv, 0, combined, 0, iv.size)
+        System.arraycopy(ciphertext, 0, combined, iv.size, ciphertext.size)
+        return ENC_PREFIX + Base64.encodeToString(combined, Base64.NO_WRAP)
+    }
+
+    /**
+     * Encrypt [plain] into a self-describing string: [ENC_PREFIX] + base64(iv | ciphertext).
+     *
+     * If the Keystore key has been permanently invalidated (e.g. the lock-screen credentials
+     * changed, or the entry is corrupt) the stale alias is dropped and a fresh key generated
+     * once before retrying. Any other Keystore/cipher failure is surfaced as a
+     * [GeneralSecurityException] so the caller can inform the user instead of crashing — the
+     * previous version let these propagate uncaught and take the IDE down on Save.
+     */
+    @Throws(GeneralSecurityException::class)
+    fun encrypt(plain: String): String {
+        return try {
+            encryptWith(getOrCreateKey(), plain)
+        } catch (e: KeyPermanentlyInvalidatedException) {
+            Log.w(TAG, "Keystore key invalidated; regenerating and retrying encrypt", e)
+            deleteKey()
+            encryptWith(getOrCreateKey(), plain)
+        }
+    }
+
+    /**
+     * Return the plaintext for a stored value, handling both formats transparently:
+     * an [ENC_PREFIX] value is decrypted; anything else is returned unchanged as
+     * legacy plaintext (it gets migrated to ciphertext on the next save). Returns
+     * null if a ciphertext value can't be decrypted — e.g. the Keystore key was
+     * lost or invalidated — in which case the user must re-enter the key.
+     */
+    fun decrypt(stored: String?): String? {
+        if (stored == null) return null
+        if (!stored.startsWith(ENC_PREFIX)) return stored
+        return try {
+            val combined = Base64.decode(stored.removePrefix(ENC_PREFIX), Base64.NO_WRAP)
+            val iv = combined.copyOfRange(0, IV_LEN)
+            val ciphertext = combined.copyOfRange(IV_LEN, combined.size)
+            val cipher = Cipher.getInstance(TRANSFORM)
+            cipher.init(Cipher.DECRYPT_MODE, getOrCreateKey(), GCMParameterSpec(TAG_BITS, iv))
+            String(cipher.doFinal(ciphertext), Charsets.UTF_8)
+        } catch (e: Exception) {
+            Log.w(TAG, "Failed to decrypt stored API key", e)
+            null
+        }
+    }
+}
diff --git a/ai-assistant/src/main/kotlin/com/itsaky/androidide/plugins/aiassistant/viewmodel/AiSettingsViewModel.kt b/ai-assistant/src/main/kotlin/com/itsaky/androidide/plugins/aiassistant/viewmodel/AiSettingsViewModel.kt
index 0ca9b3c1..22ea0c41 100644
--- a/ai-assistant/src/main/kotlin/com/itsaky/androidide/plugins/aiassistant/viewmodel/AiSettingsViewModel.kt
+++ b/ai-assistant/src/main/kotlin/com/itsaky/androidide/plugins/aiassistant/viewmodel/AiSettingsViewModel.kt
@@ -5,6 +5,7 @@ import androidx.lifecycle.LiveData
 import androidx.lifecycle.MutableLiveData
 import androidx.lifecycle.ViewModel
 import androidx.lifecycle.viewModelScope
+import com.itsaky.androidide.plugins.aiassistant.security.SecureApiKeyStore
 import com.itsaky.androidide.plugins.services.LlmInferenceService
 import com.itsaky.androidide.plugins.services.SharedServices
 import kotlinx.coroutines.Dispatchers
@@ -188,21 +189,33 @@ class AiSettingsViewModel(
     }
 
     /**
-     * Persists the Gemini API key in this plugin's private SharedPreferences.
-     * The store is app-sandboxed (not world-readable) but NOT encrypted at rest;
-     * it is recoverable on a rooted/compromised device. Use [clearGeminiApiKey]
-     * to remove it. See the plugin README "Security" section for the tradeoff.
+     * Persists the Gemini API key in this plugin's private SharedPreferences,
+     * encrypted at rest with a hardware-backed Android Keystore secret (see
+     * [SecureApiKeyStore]). Only ciphertext is written, so the prefs file alone
+     * (root, `adb backup`, forensic dump) does not disclose the key. Use
+     * [clearGeminiApiKey] to remove it.
+     *
+     * Returns false (persisting nothing) if encryption fails — e.g. a hardware Keystore
+     * fault the automatic key-regeneration retry couldn't recover — so the caller can warn
+     * the user instead of the whole IDE crashing on Save.
      */
-    fun saveGeminiApiKey(apiKey: String) {
+    fun saveGeminiApiKey(apiKey: String): Boolean {
+        val encrypted = try {
+            SecureApiKeyStore.encrypt(apiKey.trim())
+        } catch (e: Exception) {
+            android.util.Log.e(TAG, "Failed to encrypt Gemini API key", e)
+            return false
+        }
         getPluginPrefs()?.edit()?.apply {
-            putString("gemini_api_key", apiKey)
+            putString("gemini_api_key", encrypted)
             putLong("gemini_api_key_timestamp", System.currentTimeMillis())
             apply()
         }
+        return true
     }
 
     fun getGeminiApiKey(): String? {
-        return getPluginPrefs()?.getString("gemini_api_key", null)
+        return SecureApiKeyStore.decrypt(getPluginPrefs()?.getString("gemini_api_key", null))
     }
 
     fun getGeminiApiKeySaveTimestamp(): Long {
diff --git a/ai-assistant/src/main/res/drawable/ic_check.xml b/ai-assistant/src/main/res/drawable/ic_check.xml
new file mode 100644
index 00000000..9368bf87
--- /dev/null
+++ b/ai-assistant/src/main/res/drawable/ic_check.xml
@@ -0,0 +1,10 @@
+<vector xmlns:android="http://schemas.android.com/apk/res/android"
+    android:width="24dp"
+    android:height="24dp"
+    android:viewportWidth="24"
+    android:viewportHeight="24"
+    android:tint="?attr/colorPrimary">
+  <path
+      android:fillColor="@android:color/white"
+      android:pathData="M9,16.17L4.83,12l-1.42,1.41L9,19 21,7l-1.41,-1.41z"/>
+</vector>
diff --git a/ai-assistant/src/main/res/drawable/ic_file.xml b/ai-assistant/src/main/res/drawable/ic_file.xml
new file mode 100644
index 00000000..f239f312
--- /dev/null
+++ b/ai-assistant/src/main/res/drawable/ic_file.xml
@@ -0,0 +1,10 @@
+<vector xmlns:android="http://schemas.android.com/apk/res/android"
+    android:width="24dp"
+    android:height="24dp"
+    android:viewportWidth="24"
+    android:viewportHeight="24"
+    android:tint="?attr/colorControlNormal">
+  <path
+      android:fillColor="@android:color/white"
+      android:pathData="M14,2H6c-1.1,0 -1.99,0.9 -1.99,2L4,20c0,1.1 0.89,2 1.99,2H18c1.1,0 2,-0.9 2,-2V8l-6,-6zM16,18H8v-2h8v2zM16,14H8v-2h8v2zM13,9V3.5L18.5,9H13z"/>
+</vector>
diff --git a/ai-assistant/src/main/res/drawable/ic_folder.xml b/ai-assistant/src/main/res/drawable/ic_folder.xml
new file mode 100644
index 00000000..dc6b0802
--- /dev/null
+++ b/ai-assistant/src/main/res/drawable/ic_folder.xml
@@ -0,0 +1,10 @@
+<vector xmlns:android="http://schemas.android.com/apk/res/android"
+    android:width="24dp"
+    android:height="24dp"
+    android:viewportWidth="24"
+    android:viewportHeight="24"
+    android:tint="?attr/colorControlNormal">
+  <path
+      android:fillColor="@android:color/white"
+      android:pathData="M10,4H4c-1.1,0 -1.99,0.9 -1.99,2L2,18c0,1.1 0.9,2 2,2h16c1.1,0 2,-0.9 2,-2V8c0,-1.1 -0.9,-2 -2,-2h-8l-2,-2z"/>
+</vector>
diff --git a/ai-assistant/src/main/res/drawable/ic_visibility.xml b/ai-assistant/src/main/res/drawable/ic_visibility.xml
new file mode 100644
index 00000000..a3e222a2
--- /dev/null
+++ b/ai-assistant/src/main/res/drawable/ic_visibility.xml
@@ -0,0 +1,10 @@
+<vector xmlns:android="http://schemas.android.com/apk/res/android"
+    android:width="24dp"
+    android:height="24dp"
+    android:viewportWidth="24"
+    android:viewportHeight="24"
+    android:tint="?attr/colorControlNormal">
+  <path
+      android:fillColor="@android:color/white"
+      android:pathData="M12,4.5C7,4.5 2.73,7.61 1,12c1.73,4.39 6,7.5 11,7.5s9.27,-3.11 11,-7.5c-1.73,-4.39 -6,-7.5 -11,-7.5zM12,17c-2.76,0 -5,-2.24 -5,-5s2.24,-5 5,-5 5,2.24 5,5 -2.24,5 -5,5zM12,9c-1.66,0 -3,1.34 -3,3s1.34,3 3,3 3,-1.34 3,-3 -1.34,-3 -3,-3z"/>
+</vector>
diff --git a/ai-assistant/src/main/res/drawable/ic_visibility_off.xml b/ai-assistant/src/main/res/drawable/ic_visibility_off.xml
new file mode 100644
index 00000000..92c48569
--- /dev/null
+++ b/ai-assistant/src/main/res/drawable/ic_visibility_off.xml
@@ -0,0 +1,10 @@
+<vector xmlns:android="http://schemas.android.com/apk/res/android"
+    android:width="24dp"
+    android:height="24dp"
+    android:viewportWidth="24"
+    android:viewportHeight="24"
+    android:tint="?attr/colorControlNormal">
+  <path
+      android:fillColor="@android:color/white"
+      android:pathData="M12,7c2.76,0 5,2.24 5,5 0,0.65 -0.13,1.26 -0.36,1.83l2.92,2.92c1.51,-1.26 2.7,-2.89 3.43,-4.75 -1.73,-4.39 -6,-7.5 -11,-7.5 -1.4,0 -2.74,0.25 -3.98,0.7l2.16,2.16C10.74,7.13 11.35,7 12,7zM2,4.27l2.28,2.28 0.46,0.46C3.08,8.3 1.78,10.02 1,12c1.73,4.39 6,7.5 11,7.5 1.55,0 3.03,-0.3 4.38,-0.84l0.42,0.42L19.73,22 21,20.73 3.27,3 2,4.27zM7.53,9.8l1.55,1.55c-0.05,0.21 -0.08,0.43 -0.08,0.65 0,1.66 1.34,3 3,3 0.22,0 0.44,-0.03 0.65,-0.08l1.55,1.55c-0.67,0.33 -1.41,0.53 -2.2,0.53 -2.76,0 -5,-2.24 -5,-5 0,-0.79 0.2,-1.53 0.53,-2.2zM11.84,9.02l3.15,3.15 0.02,-0.16c0,-1.66 -1.34,-3 -3,-3l-0.17,0.01z"/>
+</vector>
diff --git a/ai-assistant/src/main/res/layout/item_file_picker.xml b/ai-assistant/src/main/res/layout/item_file_picker.xml
new file mode 100644
index 00000000..20efc497
--- /dev/null
+++ b/ai-assistant/src/main/res/layout/item_file_picker.xml
@@ -0,0 +1,34 @@
+<?xml version="1.0" encoding="utf-8"?>
+<LinearLayout xmlns:android="http://schemas.android.com/apk/res/android"
+    android:layout_width="match_parent"
+    android:layout_height="wrap_content"
+    android:minHeight="48dp"
+    android:gravity="center_vertical"
+    android:orientation="horizontal"
+    android:paddingHorizontal="16dp"
+    android:paddingVertical="12dp">
+
+    <ImageView
+        android:id="@+id/file_picker_row_icon"
+        android:layout_width="24dp"
+        android:layout_height="24dp"
+        android:importantForAccessibility="no" />
+
+    <TextView
+        android:id="@+id/file_picker_row_name"
+        android:layout_width="0dp"
+        android:layout_height="wrap_content"
+        android:layout_weight="1"
+        android:layout_marginStart="16dp"
+        android:textAppearance="?attr/textAppearanceBodyLarge"
+        android:textColor="?attr/colorOnSurface" />
+
+    <ImageView
+        android:id="@+id/file_picker_row_check"
+        android:layout_width="24dp"
+        android:layout_height="24dp"
+        android:layout_marginStart="8dp"
+        android:src="@drawable/ic_check"
+        android:importantForAccessibility="no"
+        android:visibility="gone" />
+</LinearLayout>
diff --git a/ai-assistant/src/main/res/layout/layout_settings_gemini_api.xml b/ai-assistant/src/main/res/layout/layout_settings_gemini_api.xml
index 179cbb56..5a5819b7 100644
--- a/ai-assistant/src/main/res/layout/layout_settings_gemini_api.xml
+++ b/ai-assistant/src/main/res/layout/layout_settings_gemini_api.xml
@@ -27,13 +27,33 @@
             android:textAppearance="?android:attr/textAppearanceSmall"
             android:paddingBottom="4dp"/>
 
-        <EditText
-            android:id="@+id/gemini_api_key_input"
+        <LinearLayout
             android:layout_width="match_parent"
             android:layout_height="wrap_content"
-            android:inputType="textPassword"
-            android:hint="Enter your Gemini API key"
-            android:maxLines="1" />
+            android:gravity="center_vertical"
+            android:orientation="horizontal">
+
+            <EditText
+                android:id="@+id/gemini_api_key_input"
+                android:layout_width="0dp"
+                android:layout_height="wrap_content"
+                android:layout_weight="1"
+                android:inputType="textPassword"
+                android:hint="@string/hint_gemini_api_key"
+                android:maxLines="1" />
+
+            <ImageButton
+                android:id="@+id/btn_toggle_api_key_visibility"
+                android:layout_width="wrap_content"
+                android:layout_height="wrap_content"
+                android:layout_marginStart="4dp"
+                android:background="?android:attr/selectableItemBackgroundBorderless"
+                android:contentDescription="@string/cd_show_api_key"
+                android:minWidth="0dp"
+                android:minHeight="0dp"
+                android:padding="4dp"
+                android:src="@drawable/ic_visibility" />
+        </LinearLayout>
     </LinearLayout>
 
     <LinearLayout
diff --git a/ai-assistant/src/main/res/values/strings.xml b/ai-assistant/src/main/res/values/strings.xml
index b9695d93..c199a12a 100644
--- a/ai-assistant/src/main/res/values/strings.xml
+++ b/ai-assistant/src/main/res/values/strings.xml
@@ -92,6 +92,15 @@
 
     <!-- Settings -->
     <string name="settings_title">AI Settings</string>
+    <string name="cd_show_api_key">Show API key</string>
+    <string name="cd_hide_api_key">Hide API key</string>
+    <string name="hint_gemini_api_key">Enter your Gemini API key</string>
+    <string name="msg_api_key_saved">API Key saved</string>
+    <string name="msg_api_key_saved_on">API Key saved on: %s</string>
+    <string name="msg_api_key_is_saved">API Key is saved</string>
+    <string name="msg_api_key_empty">API Key cannot be empty</string>
+    <string name="msg_api_key_cleared">API Key cleared</string>
+    <string name="msg_api_key_save_failed">Couldn\'t save the API key on this device. Please try again.</string>
     <string name="settings_backend">Backend</string>
     <string name="settings_model">Model</string>
     <string name="settings_temperature">Temperature</string>
@@ -105,4 +114,11 @@
     <string name="experimental_ai_use_at_your_own_risk">⚠️ Experimental AI. Use at your own risk.</string>
     <string name="current_ai_backend">Current AI backend</string>
     <string name="send">Send</string>
+
+    <!-- File picker -->
+    <string name="file_picker_title">Select Files</string>
+    <string name="file_picker_title_current">Select Files: %s</string>
+    <string name="file_picker_add_selected">Add Selected</string>
+    <string name="file_picker_toggle_all">Toggle All</string>
+    <string name="file_picker_error_not_found">Project directory not found</string>
 </resources>
diff --git a/ai-core/src/main/kotlin/com/itsaky/androidide/plugins/aicore/GeminiBackend.kt b/ai-core/src/main/kotlin/com/itsaky/androidide/plugins/aicore/GeminiBackend.kt
index 081488b8..a15ec634 100644
--- a/ai-core/src/main/kotlin/com/itsaky/androidide/plugins/aicore/GeminiBackend.kt
+++ b/ai-core/src/main/kotlin/com/itsaky/androidide/plugins/aicore/GeminiBackend.kt
@@ -73,7 +73,8 @@ class GeminiBackend(private val context: PluginContext) : LlmBackend {
             context.logger.error("GeminiBackend: Error getting preferences", e)
             null
         }
-        return prefs?.getString("gemini_api_key", null)?.trim()?.takeIf { it.isNotBlank() }
+        val stored = prefs?.getString("gemini_api_key", null)
+        return SecureApiKeyStore.decrypt(stored)?.trim()?.takeIf { it.isNotBlank() }
     }
 
     override fun getId(): String = "gemini"
@@ -81,7 +82,7 @@ class GeminiBackend(private val context: PluginContext) : LlmBackend {
     override fun getName(): String = "Gemini API"
 
     override fun isAvailable(): Boolean {
-        // Available once an API key is configured.
+        // Available once a (decryptable) API key is configured.
         val apiKey = readGeminiApiKey()
         context.logger.debug("GeminiBackend.isAvailable() - API key configured: ${!apiKey.isNullOrBlank()}")
         return !apiKey.isNullOrBlank()
diff --git a/ai-core/src/main/kotlin/com/itsaky/androidide/plugins/aicore/SecureApiKeyStore.kt b/ai-core/src/main/kotlin/com/itsaky/androidide/plugins/aicore/SecureApiKeyStore.kt
new file mode 100644
index 00000000..1e31a7fc
--- /dev/null
+++ b/ai-core/src/main/kotlin/com/itsaky/androidide/plugins/aicore/SecureApiKeyStore.kt
@@ -0,0 +1,114 @@
+package com.itsaky.androidide.plugins.aicore
+
+import android.security.keystore.KeyGenParameterSpec
+import android.security.keystore.KeyPermanentlyInvalidatedException
+import android.security.keystore.KeyProperties
+import android.util.Base64
+import android.util.Log
+import java.security.GeneralSecurityException
+import java.security.KeyStore
+import javax.crypto.Cipher
+import javax.crypto.KeyGenerator
+import javax.crypto.SecretKey
+import javax.crypto.spec.GCMParameterSpec
+
+/**
+ * AES/GCM encryption for sensitive settings (currently the Gemini API key),
+ * keyed by a hardware-backed Android Keystore secret. Only ciphertext is
+ * written to SharedPreferences, so a copied prefs file (root, `adb backup`,
+ * forensic dump) is useless without this device's Keystore.
+ *
+ * The alias and transform below are mirrored verbatim in ai-assistant's
+ * `SecureApiKeyStore` so a key written there can be decrypted here — both
+ * plugins run in the host app's process (same UID) and therefore share one
+ * Android Keystore. Keep the two copies in sync.
+ */
+object SecureApiKeyStore {
+    private const val TAG = "SecureApiKeyStore"
+    private const val KEYSTORE = "AndroidKeyStore"
+    private const val ALIAS = "cotg_ai_gemini_key_v1"
+    private const val TRANSFORM = "AES/GCM/NoPadding"
+    private const val IV_LEN = 12
+    private const val TAG_BITS = 128
+
+    /** Marks a stored value as ciphertext; anything without it is treated as legacy plaintext. */
+    const val ENC_PREFIX = "enc:v1:"
+
+    private fun getOrCreateKey(): SecretKey {
+        val ks = KeyStore.getInstance(KEYSTORE).apply { load(null) }
+        (ks.getEntry(ALIAS, null) as? KeyStore.SecretKeyEntry)?.let { return it.secretKey }
+        val generator = KeyGenerator.getInstance(KeyProperties.KEY_ALGORITHM_AES, KEYSTORE)
+        generator.init(
+            KeyGenParameterSpec.Builder(
+                ALIAS,
+                KeyProperties.PURPOSE_ENCRYPT or KeyProperties.PURPOSE_DECRYPT
+            )
+                .setBlockModes(KeyProperties.BLOCK_MODE_GCM)
+                .setEncryptionPaddings(KeyProperties.ENCRYPTION_PADDING_NONE)
+                .build()
+        )
+        return generator.generateKey()
+    }
+
+    private fun deleteKey() {
+        try {
+            KeyStore.getInstance(KEYSTORE).apply { load(null) }.deleteEntry(ALIAS)
+        } catch (e: Exception) {
+            Log.w(TAG, "Failed to delete Keystore alias $ALIAS", e)
+        }
+    }
+
+    private fun encryptWith(key: SecretKey, plain: String): String {
+        val cipher = Cipher.getInstance(TRANSFORM)
+        cipher.init(Cipher.ENCRYPT_MODE, key)
+        val iv = cipher.iv
+        val ciphertext = cipher.doFinal(plain.toByteArray(Charsets.UTF_8))
+        val combined = ByteArray(iv.size + ciphertext.size)
+        System.arraycopy(iv, 0, combined, 0, iv.size)
+        System.arraycopy(ciphertext, 0, combined, iv.size, ciphertext.size)
+        return ENC_PREFIX + Base64.encodeToString(combined, Base64.NO_WRAP)
+    }
+
+    /**
+     * Encrypt [plain] into a self-describing string: [ENC_PREFIX] + base64(iv | ciphertext).
+     *
+     * If the Keystore key has been permanently invalidated (e.g. the lock-screen credentials
+     * changed, or the entry is corrupt) the stale alias is dropped and a fresh key generated
+     * once before retrying. Any other Keystore/cipher failure is surfaced as a
+     * [GeneralSecurityException] so the caller can inform the user instead of crashing — the
+     * previous version let these propagate uncaught and take the IDE down on Save.
+     */
+    @Throws(GeneralSecurityException::class)
+    fun encrypt(plain: String): String {
+        return try {
+            encryptWith(getOrCreateKey(), plain)
+        } catch (e: KeyPermanentlyInvalidatedException) {
+            Log.w(TAG, "Keystore key invalidated; regenerating and retrying encrypt", e)
+            deleteKey()
+            encryptWith(getOrCreateKey(), plain)
+        }
+    }
+
+    /**
+     * Return the plaintext for a stored value, handling both formats transparently:
+     * an [ENC_PREFIX] value is decrypted; anything else is returned unchanged as
+     * legacy plaintext (it gets migrated to ciphertext on the next save). Returns
+     * null if a ciphertext value can't be decrypted — e.g. the Keystore key was
+     * lost or invalidated — in which case the user must re-enter the key.
+     */
+    fun decrypt(stored: String?): String? {
+        if (stored == null) return null
+        if (!stored.startsWith(ENC_PREFIX)) return stored
+        return try {
+            val combined = Base64.decode(stored.removePrefix(ENC_PREFIX), Base64.NO_WRAP)
+            val iv = combined.copyOfRange(0, IV_LEN)
+            val ciphertext = combined.copyOfRange(IV_LEN, combined.size)
+            val cipher = Cipher.getInstance(TRANSFORM)
+            cipher.init(Cipher.DECRYPT_MODE, getOrCreateKey(), GCMParameterSpec(TAG_BITS, iv))
+            String(cipher.doFinal(ciphertext), Charsets.UTF_8)
+        } catch (e: Exception) {
+            Log.w(TAG, "Failed to decrypt stored API key", e)
+            null
+        }
+    }
+}

From b44608f97cbc78e820e2abfb108cd2191d4aef64 Mon Sep 17 00:00:00 2001
From: John Trujillo <johnandrestrujillo@gmail.com>
Date: Thu, 23 Jul 2026 15:23:33 -0500
Subject: [PATCH 2/2] fix(ai-assistant): move Gemini API-key crypto off UI
 thread and harden file-picker containment

Make save/getGeminiApiKey suspend on ioDispatcher, guard edit/save UI with try-finally and confine the picker via normalized Path.startsWith with filtered, off-thread listing.
---
 .../fragments/AiSettingsFragment.kt           | 72 ++++++++++++-------
 .../fragments/FilePickerDialogFragment.kt     | 11 +--
 .../viewmodel/AiSettingsViewModel.kt          | 29 ++++----
 3 files changed, 70 insertions(+), 42 deletions(-)

diff --git a/ai-assistant/src/main/kotlin/com/itsaky/androidide/plugins/aiassistant/fragments/AiSettingsFragment.kt b/ai-assistant/src/main/kotlin/com/itsaky/androidide/plugins/aiassistant/fragments/AiSettingsFragment.kt
index 8c0686a4..76ba11a8 100644
--- a/ai-assistant/src/main/kotlin/com/itsaky/androidide/plugins/aiassistant/fragments/AiSettingsFragment.kt
+++ b/ai-assistant/src/main/kotlin/com/itsaky/androidide/plugins/aiassistant/fragments/AiSettingsFragment.kt
@@ -14,6 +14,7 @@ import android.widget.*
 import androidx.activity.result.contract.ActivityResultContracts
 import androidx.fragment.app.DialogFragment
 import androidx.lifecycle.ViewModelProvider
+import androidx.lifecycle.lifecycleScope
 import com.itsaky.androidide.plugins.PluginContext
 import com.itsaky.androidide.plugins.aiassistant.AiAssistantPlugin
 import com.itsaky.androidide.plugins.aiassistant.R
@@ -23,6 +24,7 @@ import com.itsaky.androidide.plugins.aiassistant.viewmodel.AiBackend
 import com.itsaky.androidide.plugins.aiassistant.viewmodel.AiSettingsViewModel
 import com.itsaky.androidide.plugins.aiassistant.viewmodel.EngineState
 import com.itsaky.androidide.plugins.aiassistant.viewmodel.ModelLoadingState
+import kotlinx.coroutines.launch
 import java.text.SimpleDateFormat
 import java.util.Date
 import java.util.Locale
@@ -321,19 +323,14 @@ class AiSettingsFragment : DialogFragment() {
             }
         }
 
-        val savedApiKey = viewModel.getGeminiApiKey()
-        if (savedApiKey.isNullOrBlank()) {
-            updateUiState(isEditing = true)
-            apiKeyInput.setText("")
-        } else {
-            updateUiState(isEditing = false)
-            val timestamp = viewModel.getGeminiApiKeySaveTimestamp()
-            if (timestamp > 0) {
-                val sdf = SimpleDateFormat("MMMM d, yyyy", Locale.getDefault())
-                val savedDate = sdf.format(Date(timestamp))
-                statusTextView.text = getString(R.string.msg_api_key_saved_on, savedDate)
+        viewLifecycleOwner.lifecycleScope.launch {
+            val savedApiKey = viewModel.getGeminiApiKey()
+            val hasKey = !savedApiKey.isNullOrBlank()
+            updateUiState(isEditing = !hasKey)
+            if (hasKey) {
+                statusTextView.text = savedApiKeyStatusText()
             } else {
-                statusTextView.text = getString(R.string.msg_api_key_is_saved)
+                apiKeyInput.setText("")
             }
         }
 
@@ -370,27 +367,46 @@ class AiSettingsFragment : DialogFragment() {
                 Toast.makeText(requireContext(), getString(R.string.msg_api_key_empty), Toast.LENGTH_SHORT).show()
                 return@setOnClickListener
             }
-            if (!viewModel.saveGeminiApiKey(apiKey)) {
-                Toast.makeText(requireContext(), getString(R.string.msg_api_key_save_failed), Toast.LENGTH_LONG).show()
-                return@setOnClickListener
+            saveButton.isEnabled = false
+            viewLifecycleOwner.lifecycleScope.launch {
+                val saved = try {
+                    viewModel.saveGeminiApiKey(apiKey)
+                } finally {
+                    saveButton.isEnabled = true
+                }
+                if (!saved) {
+                    Toast.makeText(requireContext(), getString(R.string.msg_api_key_save_failed), Toast.LENGTH_LONG).show()
+                    return@launch
+                }
+                Toast.makeText(requireContext(), getString(R.string.msg_api_key_saved), Toast.LENGTH_SHORT).show()
+                updateUiState(isEditing = false)
+                statusTextView.text = savedApiKeyStatusText()
             }
-            Toast.makeText(requireContext(), getString(R.string.msg_api_key_saved), Toast.LENGTH_SHORT).show()
-
-            updateUiState(isEditing = false)
-            val timestamp = viewModel.getGeminiApiKeySaveTimestamp()
-            val sdf = SimpleDateFormat("MMMM d, yyyy", Locale.getDefault())
-            val savedDate = sdf.format(Date(timestamp))
-            statusTextView.text = getString(R.string.msg_api_key_saved_on, savedDate)
         }
 
-        editButton.setOnClickListener {
+        // Reveal the (already-fetched) key in an editable, focused field. Kept separate from
+        // the click handler so the listener does one thing: fetch, then hand off.
+        fun revealEditMode(apiKey: String) {
+            apiKeyInput.setText(apiKey)
+            apiKeyInput.setSelection(apiKey.length)
             updateUiState(isEditing = true)
-            apiKeyInput.setText(viewModel.getGeminiApiKey().orEmpty())
             isKeyVisible = false
             applyKeyVisibility()
             apiKeyInput.requestFocus()
         }
 
+        editButton.setOnClickListener {
+            editButton.isEnabled = false
+            viewLifecycleOwner.lifecycleScope.launch {
+                val apiKey = try {
+                    viewModel.getGeminiApiKey().orEmpty()
+                } finally {
+                    editButton.isEnabled = true
+                }
+                revealEditMode(apiKey)
+            }
+        }
+
         clearButton.setOnClickListener {
             viewModel.clearGeminiApiKey()
             Toast.makeText(requireContext(), getString(R.string.msg_api_key_cleared), Toast.LENGTH_SHORT).show()
@@ -402,6 +418,14 @@ class AiSettingsFragment : DialogFragment() {
         setupGeminiModelSelection(modelContainer)
     }
 
+    /** Status line for a stored key: dated when the save time is known, generic otherwise. */
+    private fun savedApiKeyStatusText(): String {
+        val timestamp = viewModel.getGeminiApiKeySaveTimestamp()
+        if (timestamp <= 0) return getString(R.string.msg_api_key_is_saved)
+        val savedDate = SimpleDateFormat("MMMM d, yyyy", Locale.getDefault()).format(Date(timestamp))
+        return getString(R.string.msg_api_key_saved_on, savedDate)
+    }
+
     private fun createModelSelectionUi(parent: View): LinearLayout {
         val context = requireContext()
         val container = LinearLayout(context).apply {
diff --git a/ai-assistant/src/main/kotlin/com/itsaky/androidide/plugins/aiassistant/fragments/FilePickerDialogFragment.kt b/ai-assistant/src/main/kotlin/com/itsaky/androidide/plugins/aiassistant/fragments/FilePickerDialogFragment.kt
index cba1cfbb..39eb0e2f 100644
--- a/ai-assistant/src/main/kotlin/com/itsaky/androidide/plugins/aiassistant/fragments/FilePickerDialogFragment.kt
+++ b/ai-assistant/src/main/kotlin/com/itsaky/androidide/plugins/aiassistant/fragments/FilePickerDialogFragment.kt
@@ -156,6 +156,7 @@ class FilePickerDialogFragment : DialogFragment() {
         }
 
         directory.listFiles()
+            ?.filter { isWithinRoot(it) }
             ?.sortedWith(compareBy<File> { !it.isDirectory }.thenBy { it.name.lowercase() })
             ?.forEach { file -> newRows.add(FileRow(file, file.name, file.isDirectory)) }
 
@@ -194,10 +195,12 @@ class FilePickerDialogFragment : DialogFragment() {
     private fun titleFor(dir: File): String =
         getString(R.string.file_picker_title_current, dir.name)
 
-    private fun isWithinRoot(dir: File): Boolean {
-        val root = canonical(rootDirectory)
-        val path = canonical(dir)
-        return path == root || path.startsWith(root + File.separator)
+    /** True if [file] resolves (symlinks included) to a path at or below [rootDirectory]. */
+    private fun isWithinRoot(file: File): Boolean = try {
+        val root = rootDirectory.canonicalFile.toPath().normalize()
+        file.canonicalFile.toPath().normalize().startsWith(root)
+    } catch (e: Exception) {
+        false
     }
 
     private fun canonical(f: File): String =
diff --git a/ai-assistant/src/main/kotlin/com/itsaky/androidide/plugins/aiassistant/viewmodel/AiSettingsViewModel.kt b/ai-assistant/src/main/kotlin/com/itsaky/androidide/plugins/aiassistant/viewmodel/AiSettingsViewModel.kt
index 22ea0c41..eb2440e4 100644
--- a/ai-assistant/src/main/kotlin/com/itsaky/androidide/plugins/aiassistant/viewmodel/AiSettingsViewModel.kt
+++ b/ai-assistant/src/main/kotlin/com/itsaky/androidide/plugins/aiassistant/viewmodel/AiSettingsViewModel.kt
@@ -8,8 +8,11 @@ import androidx.lifecycle.viewModelScope
 import com.itsaky.androidide.plugins.aiassistant.security.SecureApiKeyStore
 import com.itsaky.androidide.plugins.services.LlmInferenceService
 import com.itsaky.androidide.plugins.services.SharedServices
+import kotlinx.coroutines.CoroutineDispatcher
 import kotlinx.coroutines.Dispatchers
 import kotlinx.coroutines.launch
+import kotlinx.coroutines.withContext
+import com.itsaky.androidide.plugins.PluginContext
 
 /**
  * State for the model file loading.
@@ -49,7 +52,8 @@ enum class AiBackend(val displayName: String) {
 data class GeminiModelOptions(val models: List<String>, val isLive: Boolean)
 
 class AiSettingsViewModel(
-    private val getContext: () -> com.itsaky.androidide.plugins.PluginContext?
+    private val getContext: () -> PluginContext?,
+    private val ioDispatcher: CoroutineDispatcher = Dispatchers.IO
 ) : ViewModel() {
 
     companion object {
@@ -189,33 +193,30 @@ class AiSettingsViewModel(
     }
 
     /**
-     * Persists the Gemini API key in this plugin's private SharedPreferences,
-     * encrypted at rest with a hardware-backed Android Keystore secret (see
-     * [SecureApiKeyStore]). Only ciphertext is written, so the prefs file alone
-     * (root, `adb backup`, forensic dump) does not disclose the key. Use
-     * [clearGeminiApiKey] to remove it.
+     * Encrypts [apiKey] via [SecureApiKeyStore] and persists only the ciphertext to private
+     * prefs, off the main thread (Keystore IPC + AES/GCM). Nothing is written on failure.
      *
-     * Returns false (persisting nothing) if encryption fails — e.g. a hardware Keystore
-     * fault the automatic key-regeneration retry couldn't recover — so the caller can warn
-     * the user instead of the whole IDE crashing on Save.
+     * @param apiKey the plaintext key to store (trimmed before encryption)
+     * @return true if the key was encrypted and persisted, false if encryption failed
      */
-    fun saveGeminiApiKey(apiKey: String): Boolean {
+    suspend fun saveGeminiApiKey(apiKey: String): Boolean = withContext(ioDispatcher) {
         val encrypted = try {
             SecureApiKeyStore.encrypt(apiKey.trim())
         } catch (e: Exception) {
             android.util.Log.e(TAG, "Failed to encrypt Gemini API key", e)
-            return false
+            return@withContext false
         }
         getPluginPrefs()?.edit()?.apply {
             putString("gemini_api_key", encrypted)
             putLong("gemini_api_key_timestamp", System.currentTimeMillis())
             apply()
         }
-        return true
+        true
     }
 
-    fun getGeminiApiKey(): String? {
-        return SecureApiKeyStore.decrypt(getPluginPrefs()?.getString("gemini_api_key", null))
+    /** Decrypt the stored key off the main thread (Keystore IPC + AES/GCM). */
+    suspend fun getGeminiApiKey(): String? = withContext(ioDispatcher) {
+        SecureApiKeyStore.decrypt(getPluginPrefs()?.getString("gemini_api_key", null))
     }
 
     fun getGeminiApiKeySaveTimestamp(): Long {