diff --git a/base/src/main/java/io/github/sds100/keymapper/base/expertmode/SystemBridgeAutoStarter.kt b/base/src/main/java/io/github/sds100/keymapper/base/expertmode/SystemBridgeAutoStarter.kt
index c54298cffa..0cdd5a1611 100644
--- a/base/src/main/java/io/github/sds100/keymapper/base/expertmode/SystemBridgeAutoStarter.kt
+++ b/base/src/main/java/io/github/sds100/keymapper/base/expertmode/SystemBridgeAutoStarter.kt
@@ -284,6 +284,7 @@ class SystemBridgeAutoStarter @Inject constructor(
         // Otherwise, it may not autostart on reboot if it started earlier than when it last auto
         // started relative to the last boot.
         preferences.set(Keys.systemBridgeLastAutoStartTime, clock.unixTimestamp())
+        preferences.set(Keys.systemBridgeLastAutoStartBootTime, bootTimestamp())
 
         when (type) {
             AutoStartType.ADB -> {
@@ -349,6 +350,8 @@ class SystemBridgeAutoStarter @Inject constructor(
     private suspend fun isWithinAutoStartCooldown(): Boolean {
         val lastAutoStartTime = preferences.get(Keys.systemBridgeLastAutoStartTime).first()
         val lastManualStartTime = preferences.get(Keys.systemBridgeLastManualStartTime).first()
+        val lastAutoStartBootTime =
+            preferences.get(Keys.systemBridgeLastAutoStartBootTime).first()
         val currentTime = clock.unixTimestamp()
 
         if (lastAutoStartTime == null) {
@@ -362,10 +365,31 @@ class SystemBridgeAutoStarter @Inject constructor(
             return false
         }
 
+        // If the device has rebooted since the last auto start then the system bridge stopped
+        // because of the reboot and not because it crashed. The cooldown only exists to prevent
+        // an infinite restart loop within a single boot session, so ignore it after a reboot.
+        // Otherwise rebooting twice within 5 minutes wrongly prevents the system bridge from
+        // auto starting again.
+        if (lastAutoStartBootTime != null &&
+            bootTimestamp() - lastAutoStartBootTime > REBOOT_DETECTION_TOLERANCE_SEC
+        ) {
+            return false
+        }
+
         return currentTime >= lastAutoStartTime &&
             currentTime - lastAutoStartTime < (5 * 60)
     }
 
+    /**
+     * The approximate unix time in seconds at which the device last booted, calculated from the
+     * current wall clock time minus the time elapsed since boot. This value is stable within a
+     * boot session (aside from small clock adjustments) and jumps forward when the device
+     * reboots, so it can be used to detect that a reboot has happened.
+     */
+    private fun bootTimestamp(): Long {
+        return clock.unixTimestamp() - (clock.elapsedRealtime() / 1000)
+    }
+
     private suspend fun isAutoStartEnabled(): Boolean {
         return preferences.get(Keys.isSystemBridgeKeepAliveEnabled)
             .map { it ?: PreferenceDefaults.EXPERT_MODE_KEEP_ALIVE }
@@ -451,4 +475,14 @@ class SystemBridgeAutoStarter @Inject constructor(
 
         notificationAdapter.showNotification(model)
     }
+
+    companion object {
+        /**
+         * The boot timestamp is only accurate to within a few seconds because the wall clock and
+         * elapsed realtime are not sampled at exactly the same instant and the clock may be
+         * adjusted by the system. This tolerance avoids mistaking that jitter for a reboot while
+         * still reliably detecting a real reboot, which shifts the boot timestamp far more.
+         */
+        private const val REBOOT_DETECTION_TOLERANCE_SEC = 60L
+    }
 }
diff --git a/base/src/test/java/io/github/sds100/keymapper/base/expertmode/SystemBridgeAutoStarterTest.kt b/base/src/test/java/io/github/sds100/keymapper/base/expertmode/SystemBridgeAutoStarterTest.kt
index 39f34d3b4a..9f0df80f2e 100644
--- a/base/src/test/java/io/github/sds100/keymapper/base/expertmode/SystemBridgeAutoStarterTest.kt
+++ b/base/src/test/java/io/github/sds100/keymapper/base/expertmode/SystemBridgeAutoStarterTest.kt
@@ -783,4 +783,33 @@ class SystemBridgeAutoStarterTest {
                 verify(mockConnectionManager, never()).startWithRoot()
             }
         }
+
+    @Test
+    fun `auto start within 5 minutes of the last auto start if the device rebooted in between`() =
+        runTest(testDispatcher) {
+            fakePreferences.set(Keys.isSystemBridgeKeepAliveEnabled, true)
+            fakePreferences.set(Keys.isSystemBridgeUsed, true)
+            fakePreferences.set(Keys.handledUpgradeToExpertMode, true)
+
+            // The system bridge was last auto started only 2 minutes ago, which is within the
+            // cooldown, but that was during a previous boot because the device has rebooted since.
+            fakePreferences.set(
+                Keys.systemBridgeLastAutoStartTime,
+                testScopeClock.unixTimestamp() - 120,
+            )
+            fakePreferences.set(
+                Keys.systemBridgeLastAutoStartBootTime,
+                // Booted an hour before the current boot, i.e. the device has rebooted since.
+                testScopeClock.unixTimestamp() - testScopeClock.elapsedRealtime() / 1000 - 3600,
+            )
+            isRootGrantedFlow.value = true
+
+            inOrder(mockConnectionManager) {
+                systemBridgeAutoStarter.init()
+                advanceTimeBy(6000)
+
+                // The cooldown is skipped because the device rebooted, so it auto starts.
+                verify(mockConnectionManager).startWithRoot()
+            }
+        }
 }
diff --git a/data/src/main/java/io/github/sds100/keymapper/data/Keys.kt b/data/src/main/java/io/github/sds100/keymapper/data/Keys.kt
index 2e0ec15787..afab7ef6e6 100644
--- a/data/src/main/java/io/github/sds100/keymapper/data/Keys.kt
+++ b/data/src/main/java/io/github/sds100/keymapper/data/Keys.kt
@@ -150,6 +150,14 @@ object Keys {
         longPreferencesKey("key_system_bridge_last_manual_start_time")
     val systemBridgeLastAutoStartTime = longPreferencesKey("key_system_bridge_last_auto_start_time")
 
+    /**
+     * The unix time in seconds of the last device boot at which the system bridge was auto
+     * started. Used to detect whether the device has rebooted since the last auto start so that
+     * the auto start cooldown is not applied after a reboot.
+     */
+    val systemBridgeLastAutoStartBootTime =
+        longPreferencesKey("key_system_bridge_last_auto_start_boot_time")
+
     val keyEventActionsUseSystemBridge =
         booleanPreferencesKey("key_key_event_actions_use_system_bridge")