diff --git a/sshlib/src/main/kotlin/org/connectbot/sshlib/client/SessionChannel.kt b/sshlib/src/main/kotlin/org/connectbot/sshlib/client/SessionChannel.kt
index 52ce970a..80245e0a 100644
--- a/sshlib/src/main/kotlin/org/connectbot/sshlib/client/SessionChannel.kt
+++ b/sshlib/src/main/kotlin/org/connectbot/sshlib/client/SessionChannel.kt
@@ -422,28 +422,36 @@ class SessionChannel internal constructor(
     private fun startChaffLoopIfNeeded(obs: KeystrokeObfuscator) {
         if (chaffJob?.isActive == true) return
         chaffJob = connectionScope.launch {
-            while (obfuscatorMutex.withLock { obs.isActive() }) {
-                val delayMs = obfuscatorMutex.withLock {
-                    obs.delayUntilNextSendMs()
-                }
-                if (delayMs > 0) {
-                    delay(delayMs)
-                }
-                val shouldSendChaff = obfuscatorMutex.withLock {
-                    if (!obs.isActive()) {
-                        false
-                    } else if (pendingObfuscatedWrites.get() > 0) {
-                        null
-                    } else {
-                        obs.advanceInterval()
-                        true
+            try {
+                while (obfuscatorMutex.withLock { obs.isActive() }) {
+                    val delayMs = obfuscatorMutex.withLock {
+                        obs.delayUntilNextSendMs()
+                    }
+                    if (delayMs > 0) {
+                        delay(delayMs)
+                    }
+                    val shouldSendChaff = obfuscatorMutex.withLock {
+                        if (!obs.isActive()) {
+                            false
+                        } else if (pendingObfuscatedWrites.get() > 0) {
+                            null
+                        } else {
+                            obs.advanceInterval()
+                            true
+                        }
+                    }
+                    when (shouldSendChaff) {
+                        true -> connection.sendChaff()
+                        false -> break
+                        null -> obfuscatedWritesIdle.receiveCatching()
                     }
                 }
-                when (shouldSendChaff) {
-                    true -> connection.sendChaff()
-                    false -> break
-                    null -> obfuscatedWritesIdle.receiveCatching()
-                }
+            } catch (cancelled: CancellationException) {
+                throw cancelled
+            } catch (failure: Exception) {
+                // An admitted packet may fail with a transport error after cancellation.
+                // Chaff has no caller to receive it; use the normal connection failure path.
+                connection.transportFailed(failure)
             }
         }
     }
diff --git a/sshlib/src/test/kotlin/org/connectbot/sshlib/client/KeystrokeObfuscationTest.kt b/sshlib/src/test/kotlin/org/connectbot/sshlib/client/KeystrokeObfuscationTest.kt
index 48c95dec..7d10aa50 100644
--- a/sshlib/src/test/kotlin/org/connectbot/sshlib/client/KeystrokeObfuscationTest.kt
+++ b/sshlib/src/test/kotlin/org/connectbot/sshlib/client/KeystrokeObfuscationTest.kt
@@ -20,15 +20,23 @@ package org.connectbot.sshlib.client
 import io.mockk.coEvery
 import io.mockk.coVerify
 import io.mockk.mockk
+import kotlinx.coroutines.CancellationException
 import kotlinx.coroutines.CompletableDeferred
+import kotlinx.coroutines.CoroutineExceptionHandler
 import kotlinx.coroutines.CoroutineScope
 import kotlinx.coroutines.ExperimentalCoroutinesApi
+import kotlinx.coroutines.NonCancellable
+import kotlinx.coroutines.SupervisorJob
+import kotlinx.coroutines.awaitCancellation
+import kotlinx.coroutines.cancel
 import kotlinx.coroutines.delay
 import kotlinx.coroutines.launch
 import kotlinx.coroutines.test.StandardTestDispatcher
 import kotlinx.coroutines.test.advanceUntilIdle
 import kotlinx.coroutines.test.currentTime
+import kotlinx.coroutines.test.runCurrent
 import kotlinx.coroutines.test.runTest
+import kotlinx.coroutines.withContext
 import org.connectbot.sshlib.HostKeyVerifier
 import org.connectbot.sshlib.PublicKey
 import org.connectbot.sshlib.crypto.AesCtrCipher
@@ -363,6 +371,126 @@ class KeystrokeObfuscationTest {
         coVerify(exactly = 0) { conn.sendChaff() }
     }
 
+    @Test
+    fun `failed chaff write reports transport failure without escaping background worker`() = runTest {
+        val uncaught = mutableListOf<Throwable>()
+        val scope = CoroutineScope(
+            SupervisorJob() + StandardTestDispatcher(testScheduler) +
+                CoroutineExceptionHandler { _, error -> uncaught += error },
+        )
+        val conn = mockk<SshConnection>(relaxed = true)
+        val failure = TransportException("Connection closed: Socket closed")
+        coEvery { conn.sendChaff() } throws failure
+        val channel = createObfuscatingChannel(
+            conn,
+            canSendChaff = true,
+            intervalMs = 20L,
+            scope = scope,
+            obfuscatorClockMs = { testScheduler.currentTime },
+            obfuscatorRandom = Random(0),
+        )
+        try {
+            channel.markPtyGranted()
+            channel.write("a".toByteArray())
+            testScheduler.advanceTimeBy(21)
+            runCurrent()
+
+            assertTrue(uncaught.isEmpty(), "Chaff must not crash its caller's process: $uncaught")
+            coVerify(exactly = 1) { conn.sendChaff() }
+            coVerify(exactly = 1) { conn.transportFailed(failure) }
+        } finally {
+            scope.cancel()
+            runCurrent()
+        }
+    }
+
+    @Test
+    fun `chaff write failing during shutdown does not escape cancelled worker`() = runTest {
+        val uncaught = mutableListOf<Throwable>()
+        val scope = CoroutineScope(
+            SupervisorJob() + StandardTestDispatcher(testScheduler) +
+                CoroutineExceptionHandler { _, error -> uncaught += error },
+        )
+        val conn = mockk<SshConnection>(relaxed = true)
+        val writing = CompletableDeferred<Unit>()
+        val finish = CompletableDeferred<Unit>()
+        val failure = TransportException("Packet writer stopped", CancellationException("Connection closed"))
+        coEvery { conn.sendChaff() } coAnswers {
+            // An admitted SSH write can finish with a transport error even after cancellation.
+            withContext(NonCancellable) {
+                writing.complete(Unit)
+                finish.await()
+                throw failure
+            }
+        }
+        val channel = createObfuscatingChannel(
+            conn,
+            canSendChaff = true,
+            intervalMs = 20L,
+            scope = scope,
+            obfuscatorClockMs = { testScheduler.currentTime },
+            obfuscatorRandom = Random(0),
+        )
+        try {
+            channel.markPtyGranted()
+            channel.write("a".toByteArray())
+            testScheduler.advanceTimeBy(21)
+            runCurrent()
+            assertTrue(writing.isCompleted)
+
+            scope.cancel()
+            finish.complete(Unit)
+            runCurrent()
+
+            assertTrue(uncaught.isEmpty(), "Shutdown must not crash its caller's process: $uncaught")
+            // Coroutine stack recovery may copy the exception and retain the original as cause.
+            coVerify(exactly = 1) { conn.transportFailed(match { it === failure || it.cause === failure }) }
+        } finally {
+            finish.complete(Unit)
+            scope.cancel()
+            runCurrent()
+        }
+    }
+
+    @Test
+    fun `normal chaff cancellation does not report transport failure`() = runTest {
+        val uncaught = mutableListOf<Throwable>()
+        val scope = CoroutineScope(
+            SupervisorJob() + StandardTestDispatcher(testScheduler) +
+                CoroutineExceptionHandler { _, error -> uncaught += error },
+        )
+        val conn = mockk<SshConnection>(relaxed = true)
+        val writing = CompletableDeferred<Unit>()
+        coEvery { conn.sendChaff() } coAnswers {
+            writing.complete(Unit)
+            awaitCancellation()
+        }
+        val channel = createObfuscatingChannel(
+            conn,
+            canSendChaff = true,
+            intervalMs = 20L,
+            scope = scope,
+            obfuscatorClockMs = { testScheduler.currentTime },
+            obfuscatorRandom = Random(0),
+        )
+        try {
+            channel.markPtyGranted()
+            channel.write("a".toByteArray())
+            testScheduler.advanceTimeBy(21)
+            runCurrent()
+            assertTrue(writing.isCompleted)
+
+            scope.cancel()
+            runCurrent()
+
+            assertTrue(uncaught.isEmpty())
+            coVerify(exactly = 0) { conn.transportFailed(any()) }
+        } finally {
+            scope.cancel()
+            runCurrent()
+        }
+    }
+
     private fun enableTestEncryption(connection: SshConnection) {
         val packetIoField = SshConnection::class.java.getDeclaredField("packetIO")
         packetIoField.isAccessible = true