diff --git a/desktopApp/src/jvmMain/kotlin/com/vitorpamplona/amethyst/desktop/Main.kt b/desktopApp/src/jvmMain/kotlin/com/vitorpamplona/amethyst/desktop/Main.kt
index 528a9d9cb..acc7c32a1 100644
--- a/desktopApp/src/jvmMain/kotlin/com/vitorpamplona/amethyst/desktop/Main.kt
+++ b/desktopApp/src/jvmMain/kotlin/com/vitorpamplona/amethyst/desktop/Main.kt
@@ -55,6 +55,7 @@ import androidx.compose.runtime.DisposableEffect
 import androidx.compose.runtime.LaunchedEffect
 import androidx.compose.runtime.collectAsState
 import androidx.compose.runtime.getValue
+import androidx.compose.runtime.key
 import androidx.compose.runtime.mutableStateOf
 import androidx.compose.runtime.remember
 import androidx.compose.runtime.rememberCoroutineScope
@@ -184,6 +185,7 @@ fun main() {
                 height = 800.dp,
                 position = WindowPosition.Aligned(Alignment.Center),
             )
+        var appRestartKey by remember { mutableStateOf(0) }
         var showComposeDialog by remember { mutableStateOf(false) }
         var replyToNote by remember { mutableStateOf<com.vitorpamplona.quartz.nip01Core.core.Event?>(null) }
         val deckScope = rememberCoroutineScope()
@@ -410,25 +412,28 @@ fun main() {
                 LocalAwtWindow provides window,
                 LocalIsImmersiveFullscreen provides immersiveFullscreenState,
             ) {
-                App(
-                    layoutMode = layoutMode,
-                    deckState = deckState,
-                    accountManager = accountManager,
-                    showComposeDialog = showComposeDialog,
-                    showAddColumnDialog = showAddColumnDialog,
-                    onShowComposeDialog = { showComposeDialog = true },
-                    onShowReplyDialog = { event ->
-                        replyToNote = event
-                        showComposeDialog = true
-                    },
-                    onDismissComposeDialog = {
-                        showComposeDialog = false
-                        replyToNote = null
-                    },
-                    onDismissAddColumnDialog = { showAddColumnDialog = false },
-                    onShowAddColumnDialog = { showAddColumnDialog = true },
-                    replyToNote = replyToNote,
-                )
+                key(appRestartKey) {
+                    App(
+                        layoutMode = layoutMode,
+                        deckState = deckState,
+                        accountManager = accountManager,
+                        showComposeDialog = showComposeDialog,
+                        showAddColumnDialog = showAddColumnDialog,
+                        onShowComposeDialog = { showComposeDialog = true },
+                        onShowReplyDialog = { event ->
+                            replyToNote = event
+                            showComposeDialog = true
+                        },
+                        onDismissComposeDialog = {
+                            showComposeDialog = false
+                            replyToNote = null
+                        },
+                        onDismissAddColumnDialog = { showAddColumnDialog = false },
+                        onShowAddColumnDialog = { showAddColumnDialog = true },
+                        replyToNote = replyToNote,
+                        onRestartApp = { appRestartKey++ },
+                    )
+                }
             }
         }
     }
@@ -447,6 +452,7 @@ fun App(
     onDismissAddColumnDialog: () -> Unit,
     onShowAddColumnDialog: () -> Unit,
     replyToNote: com.vitorpamplona.quartz.nip01Core.core.Event?,
+    onRestartApp: () -> Unit = {},
 ) {
     val localCache = remember { DesktopLocalCache() }
     val accountState by accountManager.accountState.collectAsState()
@@ -468,6 +474,14 @@ fun App(
             }
         }
 
+    // Clean up Tor daemon on unmount (key() change triggers this)
+    DisposableEffect(torManager) {
+        onDispose {
+            torManager.stopSync()
+            activeTorManager = null
+        }
+    }
+
     // Build TorRelayEvaluation for per-relay routing
     val torRelayEvaluation =
         remember(torSettings) {
@@ -606,6 +620,8 @@ fun App(
                                         .save(newSettings)
                                     torTypeFlow.value = newSettings.torType
                                     externalPortFlow.value = newSettings.externalSocksPort
+                                    // Rebuild app to apply Tor changes
+                                    onRestartApp()
                                 },
                             ),
                     ) {
diff --git a/desktopApp/src/jvmMain/kotlin/com/vitorpamplona/amethyst/desktop/ui/tor/TorSettingsDialog.kt b/desktopApp/src/jvmMain/kotlin/com/vitorpamplona/amethyst/desktop/ui/tor/TorSettingsDialog.kt
index 76f99a4c0..214be68e9 100644
--- a/desktopApp/src/jvmMain/kotlin/com/vitorpamplona/amethyst/desktop/ui/tor/TorSettingsDialog.kt
+++ b/desktopApp/src/jvmMain/kotlin/com/vitorpamplona/amethyst/desktop/ui/tor/TorSettingsDialog.kt
@@ -71,6 +71,8 @@ fun TorSettingsDialog(
 ) {
     var editSettings by remember { mutableStateOf(currentSettings) }
 
+    var showRestartConfirm by remember { mutableStateOf(false) }
+
     DialogWindow(
         onCloseRequest = onDismiss,
         title = "Tor Settings",
@@ -196,10 +198,24 @@ fun TorSettingsDialog(
                 ) {
                     TextButton(onClick = onDismiss) { Text("Cancel") }
                     Spacer(Modifier.width(8.dp))
-                    TextButton(onClick = {
-                        onSettingsChanged(editSettings)
-                        onDismiss()
-                    }) { Text("Save") }
+                    TextButton(onClick = { showRestartConfirm = true }) { Text("Save") }
+                }
+
+                if (showRestartConfirm) {
+                    androidx.compose.material3.AlertDialog(
+                        onDismissRequest = { showRestartConfirm = false },
+                        title = { Text("Restart Required") },
+                        text = { Text("Tor changes require restarting. Proceed?") },
+                        confirmButton = {
+                            TextButton(onClick = {
+                                onSettingsChanged(editSettings)
+                                onDismiss()
+                            }) { Text("Restart") }
+                        },
+                        dismissButton = {
+                            TextButton(onClick = { showRestartConfirm = false }) { Text("Cancel") }
+                        },
+                    )
                 }
             }
         }
diff --git a/desktopApp/src/jvmMain/kotlin/com/vitorpamplona/amethyst/desktop/ui/tor/TorSettingsSection.kt b/desktopApp/src/jvmMain/kotlin/com/vitorpamplona/amethyst/desktop/ui/tor/TorSettingsSection.kt
index e66e15f50..33161d667 100644
--- a/desktopApp/src/jvmMain/kotlin/com/vitorpamplona/amethyst/desktop/ui/tor/TorSettingsSection.kt
+++ b/desktopApp/src/jvmMain/kotlin/com/vitorpamplona/amethyst/desktop/ui/tor/TorSettingsSection.kt
@@ -27,6 +27,7 @@ import androidx.compose.foundation.layout.Spacer
 import androidx.compose.foundation.layout.fillMaxWidth
 import androidx.compose.foundation.layout.height
 import androidx.compose.foundation.layout.width
+import androidx.compose.material3.AlertDialog
 import androidx.compose.material3.MaterialTheme
 import androidx.compose.material3.SegmentedButton
 import androidx.compose.material3.SegmentedButtonDefaults
@@ -58,6 +59,7 @@ fun TorSettingsSection(
     modifier: Modifier = Modifier,
 ) {
     var showDialog by remember { mutableStateOf(false) }
+    var pendingSettings by remember { mutableStateOf<TorSettings?>(null) }
 
     Column(modifier = modifier) {
         Row(
@@ -94,7 +96,7 @@ fun TorSettingsSection(
             TorType.entries.forEachIndexed { index, torType ->
                 SegmentedButton(
                     shape = SegmentedButtonDefaults.itemShape(index = index, count = TorType.entries.size),
-                    onClick = { onSettingsChanged(currentSettings.copy(torType = torType)) },
+                    onClick = { pendingSettings = currentSettings.copy(torType = torType) },
                     selected = currentSettings.torType == torType,
                 ) {
                     Text(torType.name.lowercase().replaceFirstChar { it.uppercase() })
@@ -136,4 +138,22 @@ fun TorSettingsSection(
             onDismiss = { showDialog = false },
         )
     }
+
+    // Restart confirmation dialog
+    pendingSettings?.let { settings ->
+        AlertDialog(
+            onDismissRequest = { pendingSettings = null },
+            title = { Text("Restart Required") },
+            text = { Text("Changing Tor mode requires restarting. Your session will be briefly interrupted.") },
+            confirmButton = {
+                TextButton(onClick = {
+                    onSettingsChanged(settings)
+                    pendingSettings = null
+                }) { Text("Restart") }
+            },
+            dismissButton = {
+                TextButton(onClick = { pendingSettings = null }) { Text("Cancel") }
+            },
+        )
+    }
 }