Fixed tool calling history

app/shared/src/androidMain/kotlin/iris/platform/AndroidStorage.kt

@@ -6,6 +6,7 @@ import iris.db.IrisDatabase
 
 actual fun appDataDir(): String = AndroidEnv.context.filesDir.absolutePath
 
-// The driver creates the schema in the open-helper callback (v1: no
-// migrations yet; add .sqm files + `Schema.migrate` in onUpgrade later).
+// The schema-aware driver creates the schema on first run and applies
+// pending .sqm migrations on existing DBs (e.g. v1 -> v2: the `tool`
+// table), stamping PRAGMA user_version along the way.
 actual fun createCacheDriver(): SqlDriver = AndroidSqliteDriver(IrisDatabase.Schema, AndroidEnv.context, "iris_cache.db")

app/shared/src/commonMain/kotlin/iris/data/ChatDb.kt

@@ -16,9 +16,9 @@ import iris.protocol.IrisJson
  *   the controller) so every reconciled frame survives a process death.
  * - [metaGet] / [metaPut] hold small UI state (last-viewed lane).
  *
- * Only [MessageItem]s are persisted — tool cards, live streaming state and
+ * [MessageItem]s and [ToolItem]s are persisted; live streaming state and
  * local system notices are ephemeral. Rows are JSON payloads keyed by
- * (lane, id), so the schema does not drift with [MessageItem] fields.
+ * (lane, id), so the schema does not drift with the model fields.
  *
  * All access is synchronized: the debounced save collectors run on the
  * controller scope while [dispose] may flush from the UI thread.
@@ -32,27 +32,70 @@ class ChatDb(
 
     // ── messages ──────────────────────────────────────────────────────────
 
-    /** All persisted lanes (lane key -> messages ordered by ts). */
-    fun loadLanes(): Map<String, List<MessageItem>> =
+    /** All persisted lanes (lane key -> items: messages ordered by ts with
+     *  tool cards interleaved at their anchored position). */
+    fun loadLanes(): Map<String, List<ChatItem>> =
         synchronized(lock) {
-            val lanes = linkedMapOf<String, MutableList<MessageItem>>()
+            val messages = linkedMapOf<String, MutableList<MessageItem>>()
             for (row in db.cacheQueries.allMessages().executeAsList()) {
                 val item = decodeMessage(row.payload) ?: continue
-                lanes.getOrPut(row.lane) { mutableListOf() }.add(item)
+                messages.getOrPut(row.lane) { mutableListOf() }.add(item)
+            }
+            val tools = linkedMapOf<String, MutableList<ToolItem>>()
+            for (row in db.cacheQueries.allTools().executeAsList()) {
+                val item = decodeTool(row.payload) ?: continue
+                tools.getOrPut(row.lane) { mutableListOf() }.add(item)
+            }
+            (messages.keys + tools.keys).distinct().associateWith { lane ->
+                val items: MutableList<ChatItem> = messages[lane].orEmpty().toMutableList()
+                // Insert each tool card after its anchor message (the message
+                // it followed live). Cards sharing an anchor keep their seq
+                // order; a card whose anchor is gone (deleted message) falls
+                // to the end of the lane. The lastPos cache assumes anchors
+                // are monotonically non-decreasing per lane (true for the
+                // onToolStart anchor rule: last non-streaming message) — a
+                // tool anchored to an EARLIER message processed after a
+                // later-anchored one would be misplaced.
+                val lastPos = mutableMapOf<String, Int>()
+                for (tool in tools[lane].orEmpty()) {
+                    val anchor = tool.anchorId
+                    val pos =
+                        if (anchor == null) {
+                            -1
+                        } else {
+                            lastPos.getOrPut(anchor) { items.indexOfFirst { it.id == anchor } }
+                        }
+                    if (pos >= 0) {
+                        items.add(pos + 1, tool)
+                        if (anchor != null) lastPos[anchor] = pos + 1
+                    } else {
+                        items.add(tool)
+                    }
+                }
+                items
             }
-            lanes.mapValues { it.value.toList() }
         }
 
-    /** Replace the whole message cache with [lanes] (atomic snapshot). Tool
-     *  cards and local system notices are skipped (ephemeral). */
+    /** Replace the whole message + tool cache with [lanes] (atomic snapshot).
+     *  Local system notices are skipped (ephemeral). */
     fun saveLanes(lanes: Map<String, List<ChatItem>>) {
         synchronized(lock) {
             db.transaction {
                 db.cacheQueries.clearMessages()
+                db.cacheQueries.clearTools()
                 for ((lane, items) in lanes) {
+                    var toolSeq = 0
                     for (item in items) {
-                        if (item is MessageItem && !item.isSystem) {
-                            db.cacheQueries.upsertMessage(lane, item.id, item.ts, json.encodeToString(item))
+                        when (item) {
+                            is MessageItem -> {
+                                if (!item.isSystem) {
+                                    db.cacheQueries.upsertMessage(lane, item.id, item.ts, json.encodeToString(item))
+                                }
+                            }
+
+                            is ToolItem -> {
+                                db.cacheQueries.upsertTool(lane, item.id, toolSeq++.toLong(), json.encodeToString(item))
+                            }
                         }
                     }
                 }
@@ -109,6 +152,7 @@ class ChatDb(
         synchronized(lock) {
             db.transaction {
                 db.cacheQueries.clearMessages()
+                db.cacheQueries.clearTools()
                 db.cacheQueries.clearChannels()
                 db.cacheQueries.clearMeta()
             }
@@ -122,6 +166,13 @@ class ChatDb(
             null
         }
 
+    private fun decodeTool(payload: String): ToolItem? =
+        try {
+            json.decodeFromString<ToolItem>(payload).sanitizeForRestore()
+        } catch (_: Exception) {
+            null
+        }
+
     /** A restored message is never mid-flight: a streaming bubble is
      *  finalized (the sync replay finalizes it for real on reconnect) and a
      *  pending send becomes failed (tap to retry) — the gateway never
@@ -132,4 +183,9 @@ class ChatDb(
             pending = false,
             status = if (status == MsgStatus.Pending) MsgStatus.Failed else status,
         )
+
+    /** A restored tool card is never mid-flight: an open card (the process
+     *  died before tool.end) is closed as interrupted, mirroring
+     *  [ChatStore.finalizeInterrupted]. */
+    private fun ToolItem.sanitizeForRestore(): ToolItem = if (done) this else copy(done = true, ok = false)
 }

app/shared/src/commonMain/kotlin/iris/data/ChatStore.kt

@@ -90,7 +90,13 @@ data class MediaItem(
     val localPath: String? = null,
 )
 
-/** A structured tool-activity card (spinner until [done]). */
+/** A structured tool-activity card (spinner until [done]).
+ *  [anchorId] is the id of the message this card follows in the lane (the
+ *  last non-streaming message when the tool started) — persisted with the
+ *  card so a restart restores it in its correct position (user message →
+ *  tool card → answer) instead of dropping it or appending it at the end.
+ *  [Serializable]: persisted as a JSON payload in the local cache (ChatDb). */
+@Serializable
 data class ToolItem(
     override val id: String,
     val index: Int,
@@ -102,6 +108,7 @@ data class ToolItem(
     val ok: Boolean = true,
     val duration: Double? = null,
     val outputPreview: String? = null,
+    val anchorId: String? = null,
 ) : ChatItem
 
 class ChatStore {
@@ -114,7 +121,6 @@ class ChatStore {
     val currentLane: StateFlow<String> = _currentLane.asStateFlow()
 
     private var localSeq = 0
-    private var toolSeq = 0
 
     /** When false, `message.start`/`message.update` frames are ignored and each
      *  reply materializes as a single final message on `message.stop`
@@ -169,8 +175,11 @@ class ChatStore {
         lane: String,
         media: List<MediaItem> = emptyList(),
     ): String {
-        localSeq++
-        val id = "local_$localSeq"
+        // Process-unique id: the in-memory seq resets on every ChatStore
+        // creation, and failed sends are persisted — a restart would
+        // otherwise re-mint local_1 and collide with the restored bubble
+        // (duplicate list key).
+        val id = randomId("local")
         updateLane(lane) {
             it + MessageItem(id = id, role = ROLE_USER, text = text, ts = 0, pending = true, status = MsgStatus.Pending, media = media)
         }
@@ -418,9 +427,17 @@ class ChatStore {
         frame: Frame,
     ) {
         val p = frame.payloadAs<ToolStartPayload>() ?: return
-        toolSeq++
-        val id = "tool_$toolSeq"
+        // Process-unique id: the in-memory seq resets on every ChatStore
+        // creation, and cards are persisted — a restart would otherwise
+        // re-mint tool_1 and collide with the restored card (duplicate list
+        // key, upsert overwrite). onToolProgress/onToolEnd match by index,
+        // so non-sequential ids are safe.
+        val id = randomId("tool")
         updateLane(lane) { list ->
+            // Anchor the card to the message it follows: the last non-streaming
+            // message (a live streaming bubble is the answer that arrives AFTER
+            // the tool, so it is skipped). Restored with the card on restart.
+            val anchorId = list.lastOrNull { it is MessageItem && !it.streaming }?.id
             list +
                 ToolItem(
                     id = id,
@@ -428,6 +445,7 @@ class ChatStore {
                     name = p.name,
                     preview = p.preview,
                     args = p.args,
+                    anchorId = anchorId,
                 )
         }
     }
@@ -682,9 +700,11 @@ class ChatStore {
      * Load a history page into [lane] (oldest → newest). The history is the
      * authoritative full list of final messages for the lane; it replaces the
      * lane's final messages and preserves non-final items (tool cards, live
-     * streaming bubbles, commentary) that are not part of the history. Used to
-     * restore the view on first open of a chat / after a process death, where
-     * the in-memory store is empty and the `sync` delta does not cover older
+     * streaming bubbles, commentary) that are not part of the history. Tool
+     * cards sort at their anchor message's position, so a history refresh
+     * keeps them between the user message and the answer. Used to restore the
+     * view on first open of a chat / after a process death, where the
+     * in-memory store is empty and the `sync` delta does not cover older
      * messages.
      */
     fun loadHistory(
@@ -697,8 +717,28 @@ class ChatStore {
                 list.filter { item ->
                     item !is MessageItem || item.id !in historyIds
                 }
+            // ts of every item in the current lane: ts-less items (commentary,
+            // tool cards) inherit the ts of the item before them, so a tool
+            // card anchored to a commentary still sorts at the right place.
+            val tsOf = mutableMapOf<String, Long>()
+            var lastTs = 0L
+            for (item in list) {
+                val t = (item as? MessageItem)?.ts?.takeIf { it > 0 } ?: lastTs
+                if (t > 0) lastTs = t
+                tsOf[item.id] = t
+            }
+            // History is authoritative for the ts of its messages.
+            for (m in messages) {
+                if (m.ts > 0) tsOf[m.id] = m.ts
+            }
             (messages + preserved).sortedBy { item ->
-                (item as? MessageItem)?.ts?.takeIf { it > 0 } ?: Long.MAX_VALUE
+                when (item) {
+                    is MessageItem -> item.ts.takeIf { it > 0 } ?: Long.MAX_VALUE
+
+                    // A resolved ts of 0 means the anchor itself is ts-less
+                    // (lane start) — sort with it (end) instead of to the top.
+                    is ToolItem -> tsOf[item.anchorId]?.takeIf { it > 0 } ?: Long.MAX_VALUE
+                }
             }
         }
     }
@@ -710,7 +750,7 @@ class ChatStore {
      * delta and the `history` refresh reconcile the cache on connect.
      * No-op when [lanes] is empty (first launch).
      */
-    fun loadFromCache(lanes: Map<String, List<MessageItem>>) {
+    fun loadFromCache(lanes: Map<String, List<ChatItem>>) {
         if (lanes.isEmpty()) return
         _lanes.value = lanes
     }

app/shared/src/commonMain/kotlin/iris/state/IrisController.kt

@@ -465,13 +465,24 @@ class IrisController(
             client.events.collect { frame ->
                 try {
                     when (frame.type) {
+                        TYPE_TOOL_START,
+                        TYPE_TOOL_PROGRESS,
+                        TYPE_TOOL_END,
+                        -> {
+                            // Tool cards are restored from the local cache
+                            // (anchored to their message); they are not part
+                            // of `history`. A sync replay (frame carries a
+                            // cursor) would create duplicate cards appended
+                            // AFTER the lane's restored messages — drop
+                            // them. Live tool frames (no cursor) flow through
+                            // as usual.
+                            if (frame.cursor == null) chat.onFrame(frame)
+                        }
+
                         TYPE_MESSAGE,
                         TYPE_MESSAGE_START,
                         TYPE_MESSAGE_UPDATE,
                         TYPE_MESSAGE_STOP,
-                        TYPE_TOOL_START,
-                        TYPE_TOOL_PROGRESS,
-                        TYPE_TOOL_END,
                         TYPE_COMMENTARY,
                         TYPE_MEDIA_OFFER,
                         -> {

app/shared/src/commonMain/sqldelight/iris/db/Cache.sq

@@ -11,6 +11,14 @@ CREATE TABLE message (
     PRIMARY KEY (lane, id)
 );
 
+CREATE TABLE tool (
+    lane TEXT NOT NULL, -- lane key: chatId or chatId::threadId
+    id TEXT NOT NULL, -- local tool card id (tool_N)
+    seq INTEGER NOT NULL, -- card order within the lane (lane position)
+    payload TEXT NOT NULL, -- serialized ToolItem (carries its anchor_id)
+    PRIMARY KEY (lane, id)
+);
+
 CREATE TABLE channel (
     chat_id TEXT NOT NULL PRIMARY KEY,
     payload TEXT NOT NULL -- serialized ChannelInfo
@@ -33,6 +41,18 @@ VALUES (?, ?, ?, ?);
 clearMessages:
 DELETE FROM message;
 
+allTools:
+SELECT lane, seq, payload
+FROM tool
+ORDER BY lane, seq;
+
+upsertTool:
+INSERT OR REPLACE INTO tool (lane, id, seq, payload)
+VALUES (?, ?, ?, ?);
+
+clearTools:
+DELETE FROM tool;
+
 allChannels:
 SELECT chat_id, payload
 FROM channel;

app/shared/src/commonMain/sqldelight/migrations/1.sqm

@@ -0,0 +1,9 @@
+-- v1 -> v2: persist tool cards (M-cache: tool cards survive a restart,
+-- anchored to the message they follow — see ChatDb.loadLanes).
+CREATE TABLE tool (
+    lane TEXT NOT NULL,
+    id TEXT NOT NULL,
+    seq INTEGER NOT NULL,
+    payload TEXT NOT NULL,
+    PRIMARY KEY (lane, id)
+);

app/shared/src/commonTest/kotlin/iris/data/ChatStoreCacheTest.kt

@@ -1,5 +1,9 @@
 package iris.data
 
+import iris.protocol.Frame
+import iris.protocol.IrisJson
+import iris.protocol.TYPE_TOOL_START
+import iris.protocol.ToolStartPayload
 import kotlin.test.Test
 import kotlin.test.assertEquals
 
@@ -10,13 +14,14 @@ class ChatStoreCacheTest {
         store.loadFromCache(
             mapOf(
                 "android:default" to
-                    listOf(
+                    listOf<ChatItem>(
                         MessageItem(id = "m1", role = "user", text = "hi", ts = 1),
+                        ToolItem(id = "tool_1", index = 0, name = "bash", done = true, anchorId = "m1"),
                         MessageItem(id = "m2", role = "assistant", text = "hello", ts = 2),
                     ),
             ),
         )
-        assertEquals(listOf("m1", "m2"), store.lanes.value["android:default"]!!.map { it.id })
+        assertEquals(listOf("m1", "tool_1", "m2"), store.lanes.value["android:default"]!!.map { it.id })
     }
 
     @Test
@@ -26,4 +31,83 @@ class ChatStoreCacheTest {
         store.loadFromCache(emptyMap())
         assertEquals(1, store.lanes.value["android:default"]!!.size)
     }
+
+    @Test
+    fun loadHistoryKeepsToolCardsAtAnchor() {
+        val store = ChatStore()
+        // Lane as restored from the cache: user message, tool card anchored
+        // to it, and the final answer.
+        store.loadFromCache(
+            mapOf(
+                "android:default" to
+                    listOf<ChatItem>(
+                        MessageItem(id = "m1", role = "user", text = "count", ts = 100),
+                        ToolItem(id = "tool_1", index = 0, name = "terminal", done = true, anchorId = "m1"),
+                        MessageItem(id = "m2", role = "assistant", text = "16", ts = 200),
+                    ),
+            ),
+        )
+        // A history refresh (authoritative messages, no tool cards) must keep
+        // the tool card between the user message and the answer — not push
+        // it to the end.
+        store.loadHistory(
+            "android:default",
+            listOf(
+                MessageItem(id = "m1", role = "user", text = "count", ts = 100),
+                MessageItem(id = "m2", role = "assistant", text = "16", ts = 200),
+            ),
+        )
+        assertEquals(listOf("m1", "tool_1", "m2"), store.lanes.value["android:default"]!!.map { it.id })
+    }
+
+    @Test
+    fun loadHistoryDedupesAndKeepsUnanchoredToolsLast() {
+        val store = ChatStore()
+        store.loadFromCache(
+            mapOf(
+                "android:default" to
+                    listOf<ChatItem>(
+                        MessageItem(id = "m1", role = "user", text = "count", ts = 100),
+                        ToolItem(id = "tool_1", index = 0, name = "bash", done = true),
+                    ),
+            ),
+        )
+        store.loadHistory(
+            "android:default",
+            listOf(MessageItem(id = "m1", role = "user", text = "count", ts = 100)),
+        )
+        // A card whose anchor is unknown falls to the end (degenerate case).
+        assertEquals(listOf("m1", "tool_1"), store.lanes.value["android:default"]!!.map { it.id })
+    }
+
+    @Test
+    fun toolStartIdsNeverCollideWithRestoredCards() {
+        val store = ChatStore()
+        // Lane restored from the cache after a restart, holding a persisted
+        // card minted by the PREVIOUS process.
+        store.loadFromCache(
+            mapOf(
+                "android:default" to
+                    listOf<ChatItem>(
+                        MessageItem(id = "m1", role = "user", text = "hi", ts = 1),
+                        ToolItem(id = "tool_1", index = 0, name = "bash", done = true, anchorId = "m1"),
+                    ),
+            ),
+        )
+        // A new turn must not re-mint an id the restored lane already holds
+        // (duplicate LazyColumn key / upsert overwrite under the same PK).
+        store.onFrame(
+            Frame(
+                type = TYPE_TOOL_START,
+                chatId = "android",
+                payload =
+                    IrisJson.instance.encodeToJsonElement(
+                        ToolStartPayload.serializer(),
+                        ToolStartPayload(index = 0, name = "terminal", preview = "ls"),
+                    ),
+            ),
+        )
+        val ids = store.lanes.value["android:default"]!!.map { it.id }
+        assertEquals(ids.size, ids.toSet().size)
+    }
 }

app/shared/src/desktopMain/kotlin/iris/platform/DesktopStorage.kt

@@ -4,13 +4,41 @@ import app.cash.sqldelight.db.SqlDriver
 import app.cash.sqldelight.driver.jdbc.sqlite.JdbcSqliteDriver
 import iris.db.IrisDatabase
 import java.io.File
+import java.sql.DriverManager
+import java.util.Properties
 
 actual fun appDataDir(): String = File(System.getProperty("user.home"), ".iris").apply { mkdirs() }.absolutePath
 
-actual fun createCacheDriver(): SqlDriver {
-    val driver = JdbcSqliteDriver("jdbc:sqlite:${File(appDataDir(), "iris_cache.db").absolutePath}")
-    // v1: create the schema (no migrations yet; add .sqm files +
-    // `Schema.migrate` when the schema changes).
-    IrisDatabase.Schema.create(driver)
-    return driver
+actual fun createCacheDriver(): SqlDriver = createCacheDriver(File(appDataDir(), "iris_cache.db"))
+
+/** Schema-aware driver for the cache DB at [file]: creates the schema on
+ *  first run, applies pending .sqm migrations on existing DBs (e.g. v1 ->
+ *  v2: the `tool` table), and persists the schema version (PRAGMA
+ *  user_version). */
+internal fun createCacheDriver(file: File): SqlDriver {
+    stampLegacyV1(file)
+    return JdbcSqliteDriver("jdbc:sqlite:${file.absolutePath}", Properties(), IrisDatabase.Schema)
+}
+
+/** One-time shim for pre-existing desktop cache DBs: the old code called
+ *  `Schema.create()` directly, which never stamped PRAGMA user_version — so
+ *  those files hold the v1 schema at user_version 0, which the schema-aware
+ *  driver would treat as a fresh DB and crash on (`CREATE TABLE message` on
+ *  an existing table). Stamp them as v1 so the 1 -> 2 migration runs. */
+internal fun stampLegacyV1(file: File) {
+    if (!file.exists()) return
+    DriverManager.getConnection("jdbc:sqlite:${file.absolutePath}").use { conn ->
+        val userVersion =
+            conn.createStatement().use { st ->
+                st.executeQuery("PRAGMA user_version").use { rs -> if (rs.next()) rs.getInt(1) else 0 }
+            }
+        if (userVersion != 0) return
+        val hasMessageTable =
+            conn.createStatement().use { st ->
+                st
+                    .executeQuery("SELECT 1 FROM sqlite_master WHERE type = 'table' AND name = 'message'")
+                    .use { rs -> rs.next() }
+            }
+        if (hasMessageTable) conn.createStatement().use { st -> st.execute("PRAGMA user_version = 1") }
+    }
 }

app/shared/src/desktopTest/kotlin/iris/data/CacheMigrationTest.kt

@@ -0,0 +1,97 @@
+package iris.data
+
+import iris.platform.createCacheDriver
+import java.io.File
+import java.nio.file.Files
+import java.sql.DriverManager
+import kotlin.test.Test
+import kotlin.test.assertEquals
+
+/** Migration path for pre-existing desktop cache DBs: the schema-aware
+ *  driver plus the legacy user_version-0 shim (DesktopStorage). */
+class CacheMigrationTest {
+    private val v1Schema =
+        """
+        CREATE TABLE message (
+            lane TEXT NOT NULL,
+            id TEXT NOT NULL,
+            ts INTEGER NOT NULL,
+            payload TEXT NOT NULL,
+            PRIMARY KEY (lane, id)
+        );
+        CREATE TABLE channel (
+            chat_id TEXT NOT NULL,
+            payload TEXT NOT NULL,
+            PRIMARY KEY (chat_id)
+        );
+        CREATE TABLE meta (
+            key TEXT NOT NULL,
+            value TEXT NOT NULL,
+            PRIMARY KEY (key)
+        );
+        """.trimIndent()
+
+    private fun tempDb(name: String): File = Files.createTempDirectory("iris_cache_test").toFile().let { File(it, name) }
+
+    private fun File.queryInt(sql: String): Int =
+        DriverManager.getConnection("jdbc:sqlite:$absolutePath").use { conn ->
+            conn.createStatement().use { st ->
+                st.executeQuery(sql).use { rs -> if (rs.next()) rs.getInt(1) else -1 }
+            }
+        }
+
+    private fun File.writeV1(userVersion: Int) {
+        DriverManager.getConnection("jdbc:sqlite:$absolutePath").use { conn ->
+            conn.createStatement().use { st ->
+                v1Schema
+                    .split(";")
+                    .map { it.trim() }
+                    .filter { it.isNotEmpty() }
+                    .forEach { st.execute(it) }
+                st.execute("INSERT INTO message (lane, id, ts, payload) VALUES ('l', 'm1', 1, '{}')")
+                // (row simulates a legacy DB with data; must survive migration)
+                if (userVersion > 0) st.execute("PRAGMA user_version = $userVersion")
+            }
+        }
+    }
+
+    @Test
+    fun legacyV1DbWithZeroUserVersionMigrates() {
+        val file = tempDb("legacy0.db")
+        try {
+            // The old desktop code called Schema.create() directly, which
+            // never stamped user_version: v1 tables at user_version 0.
+            file.writeV1(userVersion = 0)
+            // Must migrate (1 -> 2 via the shim), not crash on
+            // `CREATE TABLE message` against the existing table.
+            createCacheDriver(file).use { }
+            assertEquals(1, file.queryInt("SELECT COUNT(*) FROM message"))
+            assertEquals(1, file.queryInt("SELECT 1 FROM sqlite_master WHERE type = 'table' AND name = 'tool'"))
+        } finally {
+            file.parentFile?.deleteRecursively()
+        }
+    }
+
+    @Test
+    fun legacyV1DbWithStampedVersionMigrates() {
+        val file = tempDb("legacy1.db")
+        try {
+            file.writeV1(userVersion = 1)
+            createCacheDriver(file).use { }
+            assertEquals(1, file.queryInt("SELECT 1 FROM sqlite_master WHERE type = 'table' AND name = 'tool'"))
+        } finally {
+            file.parentFile?.deleteRecursively()
+        }
+    }
+
+    @Test
+    fun freshDbCreatesSchema() {
+        val file = tempDb("fresh.db")
+        try {
+            createCacheDriver(file).use { }
+            assertEquals(1, file.queryInt("SELECT 1 FROM sqlite_master WHERE type = 'table' AND name = 'tool'"))
+        } finally {
+            file.parentFile?.deleteRecursively()
+        }
+    }
+}

app/shared/src/jvmTest/kotlin/iris/data/ChatDbTest.kt

@@ -6,7 +6,9 @@ import iris.protocol.ChannelInfo
 import iris.protocol.RuntimeMeta
 import kotlin.test.Test
 import kotlin.test.assertEquals
+import kotlin.test.assertFalse
 import kotlin.test.assertNull
+import kotlin.test.assertTrue
 
 /** Cache DB round-trip tests (JDBC in-memory SQLite; shared by both host targets). */
 class ChatDbTest {
@@ -42,22 +44,80 @@ class ChatDbTest {
         db.saveLanes(
             mapOf(
                 "android:default" to
-                    listOf(
+                    listOf<ChatItem>(
                         msg("m1", ts = 100),
+                        ToolItem(id = "tool_1", index = 0, name = "bash", anchorId = "m1"),
                         msg("m2", role = "assistant", text = "hi", ts = 200),
-                        ToolItem(id = "tool_1", index = 0, name = "bash"),
                     ),
-                "android:default::thr_1" to listOf(msg("m3", ts = 300)),
+                "android:default::thr_1" to listOf<ChatItem>(msg("m3", ts = 300)),
             ),
         )
         val loaded = db.loadLanes()
         assertEquals(setOf("android:default", "android:default::thr_1"), loaded.keys)
-        // Tool cards are ephemeral — not persisted.
-        assertEquals(listOf("m1", "m2"), loaded["android:default"]!!.map { it.id })
+        // Tool cards are persisted and restored at their anchored position
+        // (after the message they follow, before the answer).
+        assertEquals(listOf("m1", "tool_1", "m2"), loaded["android:default"]!!.map { it.id })
         assertEquals(listOf("m3"), loaded["android:default::thr_1"]!!.map { it.id })
-        // Ordered by ts.
-        assertEquals(100L, loaded["android:default"]!![0].ts)
-        assertEquals(200L, loaded["android:default"]!![1].ts)
+        // Messages ordered by ts.
+        assertEquals(100L, (loaded["android:default"]!![0] as MessageItem).ts)
+        assertEquals(200L, (loaded["android:default"]!![2] as MessageItem).ts)
+    }
+
+    @Test
+    fun toolCardsShareAnchorKeepOrder() {
+        val db = newDb()
+        db.saveLanes(
+            mapOf(
+                "android:default" to
+                    listOf<ChatItem>(
+                        msg("m1", ts = 100),
+                        ToolItem(id = "tool_1", index = 0, name = "search_files", anchorId = "m1"),
+                        ToolItem(id = "tool_2", index = 1, name = "terminal", anchorId = "m1"),
+                        msg("m2", role = "assistant", ts = 200),
+                    ),
+            ),
+        )
+        assertEquals(listOf("m1", "tool_1", "tool_2", "m2"), db.loadLanes()["android:default"]!!.map { it.id })
+    }
+
+    @Test
+    fun toolCardWithMissingAnchorFallsToEnd() {
+        val db = newDb()
+        db.saveLanes(
+            mapOf(
+                "android:default" to
+                    listOf<ChatItem>(
+                        msg("m1", ts = 100),
+                        ToolItem(id = "tool_1", index = 0, name = "bash", anchorId = "deleted"),
+                        msg("m2", role = "assistant", ts = 200),
+                    ),
+            ),
+        )
+        assertEquals(listOf("m1", "m2", "tool_1"), db.loadLanes()["android:default"]!!.map { it.id })
+    }
+
+    @Test
+    fun restoreClosesOpenToolCard() {
+        val db = newDb()
+        db.saveLanes(
+            mapOf(
+                "android:default" to
+                    listOf<ChatItem>(
+                        msg("m1", ts = 100),
+                        ToolItem(id = "tool_1", index = 0, name = "bash", done = false, anchorId = "m1"),
+                        ToolItem(id = "tool_2", index = 1, name = "ls", done = true, ok = true, anchorId = "m1"),
+                    ),
+            ),
+        )
+        val lane = db.loadLanes()["android:default"]!!
+        // The process died before tool.end — the open card is closed as
+        // interrupted, not left spinning.
+        val open = lane.first { it.id == "tool_1" } as ToolItem
+        assertTrue(open.done)
+        assertFalse(open.ok)
+        // A completed card is untouched.
+        val done = lane.first { it.id == "tool_2" } as ToolItem
+        assertTrue(done.ok)
     }
 
     @Test
@@ -82,21 +142,22 @@ class ChatDbTest {
             ),
         )
         val lane = db.loadLanes()["android:default"]!!
+        val msgItem = { id: String -> lane.first { it.id == id } as MessageItem }
         // A pending send becomes failed (tap to retry); the gateway never
         // acknowledged it before the process died.
-        assertEquals(MsgStatus.Failed, lane.first { it.id == "p1" }.status)
-        assertEquals(false, lane.first { it.id == "p1" }.pending)
+        assertEquals(MsgStatus.Failed, msgItem("p1").status)
+        assertEquals(false, msgItem("p1").pending)
         // A streaming bubble is restored as finalized.
-        assertEquals(false, lane.first { it.id == "s1" }.streaming)
+        assertEquals(false, msgItem("s1").streaming)
         // Read status is preserved.
-        assertEquals(MsgStatus.Read, lane.first { it.id == "r1" }.status)
+        assertEquals(MsgStatus.Read, msgItem("r1").status)
     }
 
     @Test
     fun systemMessagesAreNotPersisted() {
         val db = newDb()
-        db.saveLanes(mapOf("android:default" to listOf(msg("sys_1", role = "system", isSystem = true))))
-        assertEquals(emptyMap<String, List<MessageItem>>(), db.loadLanes())
+        db.saveLanes(mapOf("android:default" to listOf<ChatItem>(msg("sys_1", role = "system", isSystem = true))))
+        assertTrue(db.loadLanes().isEmpty())
     }
 
     @Test
@@ -121,8 +182,8 @@ class ChatDbTest {
                         ),
                     ),
             )
-        db.saveLanes(mapOf("android:default" to listOf(item)))
-        val loaded = db.loadLanes()["android:default"]!!.first()
+        db.saveLanes(mapOf("android:default" to listOf<ChatItem>(item)))
+        val loaded = db.loadLanes()["android:default"]!!.first() as MessageItem
         assertEquals("gpt", loaded.runtime?.model)
         assertEquals("/tmp/a.png", loaded.media.first().localPath)
     }
@@ -150,10 +211,10 @@ class ChatDbTest {
         assertNull(db.metaGet("last_lane"))
         db.metaPut("last_lane", "android:chan_1")
         assertEquals("android:chan_1", db.metaGet("last_lane"))
-        db.saveLanes(mapOf("android:default" to listOf(msg("m1"))))
+        db.saveLanes(mapOf("android:default" to listOf<ChatItem>(msg("m1"))))
         db.saveChannels(listOf(ChannelInfo(chatId = "android:default", name = "General")))
         db.clearAll()
-        assertEquals(emptyMap<String, List<MessageItem>>(), db.loadLanes())
+        assertTrue(db.loadLanes().isEmpty())
         assertEquals(emptyList<ChannelInfo>(), db.loadChannels())
         assertNull(db.metaGet("last_lane"))
     }