diff --git a/okio/src/jvmMain/kotlin/okio/Timeout.kt b/okio/src/jvmMain/kotlin/okio/Timeout.kt
index 5fb88ce47e..576591ad54 100644
--- a/okio/src/jvmMain/kotlin/okio/Timeout.kt
+++ b/okio/src/jvmMain/kotlin/okio/Timeout.kt
@@ -193,10 +193,19 @@ actual open class Timeout {
 
       if (waitNanos <= 0) throw InterruptedIOException("timeout")
 
+      val cancelMarkBefore = cancelMark
+
       // Attempt to wait that long. This will return early if the monitor is notified.
       val nanosRemaining = condition.awaitNanos(waitNanos)
 
-      if (nanosRemaining <= 0) throw InterruptedIOException("timeout")
+      // If there's time remaining, we probably got the call we were waiting for.
+      if (nanosRemaining > 0) return
+
+      // Return without throwing if this timeout was canceled while we were waiting. Note that this
+      // return is a 'spurious wakeup' because Condition.signal() was not called.
+      if (cancelMark !== cancelMarkBefore) return
+
+      throw InterruptedIOException("timeout")
     } catch (e: InterruptedException) {
       Thread.currentThread().interrupt() // Retain interrupted status.
       throw InterruptedIOException("interrupted")
diff --git a/okio/src/jvmTest/kotlin/okio/AwaitSignalTest.kt b/okio/src/jvmTest/kotlin/okio/AwaitSignalTest.kt
index d8f150cb87..941791a785 100644
--- a/okio/src/jvmTest/kotlin/okio/AwaitSignalTest.kt
+++ b/okio/src/jvmTest/kotlin/okio/AwaitSignalTest.kt
@@ -21,7 +21,9 @@ import java.util.concurrent.locks.Condition
 import java.util.concurrent.locks.ReentrantLock
 import okio.TestUtil.assumeNotWindows
 import org.junit.After
-import org.junit.Assert
+import org.junit.Assert.assertEquals
+import org.junit.Assert.assertTrue
+import org.junit.Assert.fail
 import org.junit.Test
 
 class AwaitSignalTest {
@@ -57,9 +59,9 @@ class AwaitSignalTest {
     val start = now()
     try {
       timeout.awaitSignal(condition)
-      Assert.fail()
+      fail()
     } catch (expected: InterruptedIOException) {
-      Assert.assertEquals("timeout", expected.message)
+      assertEquals("timeout", expected.message)
     }
     assertElapsed(1000.0, start)
   }
@@ -72,9 +74,9 @@ class AwaitSignalTest {
     val start = now()
     try {
       timeout.awaitSignal(condition)
-      Assert.fail()
+      fail()
     } catch (expected: InterruptedIOException) {
-      Assert.assertEquals("timeout", expected.message)
+      assertEquals("timeout", expected.message)
     }
     assertElapsed(1000.0, start)
   }
@@ -88,9 +90,9 @@ class AwaitSignalTest {
     val start = now()
     try {
       timeout.awaitSignal(condition)
-      Assert.fail()
+      fail()
     } catch (expected: InterruptedIOException) {
-      Assert.assertEquals("timeout", expected.message)
+      assertEquals("timeout", expected.message)
     }
     assertElapsed(1000.0, start)
   }
@@ -104,9 +106,9 @@ class AwaitSignalTest {
     val start = now()
     try {
       timeout.awaitSignal(condition)
-      Assert.fail()
+      fail()
     } catch (expected: InterruptedIOException) {
-      Assert.assertEquals("timeout", expected.message)
+      assertEquals("timeout", expected.message)
     }
     assertElapsed(1000.0, start)
   }
@@ -119,9 +121,9 @@ class AwaitSignalTest {
     val start = now()
     try {
       timeout.awaitSignal(condition)
-      Assert.fail()
+      fail()
     } catch (expected: InterruptedIOException) {
-      Assert.assertEquals("timeout", expected.message)
+      assertEquals("timeout", expected.message)
     }
     assertElapsed(0.0, start)
   }
@@ -134,10 +136,10 @@ class AwaitSignalTest {
     Thread.currentThread().interrupt()
     try {
       timeout.awaitSignal(condition)
-      Assert.fail()
+      fail()
     } catch (expected: InterruptedIOException) {
-      Assert.assertEquals("interrupted", expected.message)
-      Assert.assertTrue(Thread.interrupted())
+      assertEquals("interrupted", expected.message)
+      assertTrue(Thread.interrupted())
     }
     assertElapsed(0.0, start)
   }
@@ -149,13 +151,60 @@ class AwaitSignalTest {
     Thread.currentThread().interrupt()
     try {
       timeout.throwIfReached()
-      Assert.fail()
+      fail()
     } catch (expected: InterruptedIOException) {
-      Assert.assertEquals("interrupted", expected.message)
-      Assert.assertTrue(Thread.interrupted())
+      assertEquals("interrupted", expected.message)
+      assertTrue(Thread.interrupted())
     }
   }
 
+  @Test
+  fun cancelBeforeWaitDoesNothing() {
+    val timeout = Timeout()
+    timeout.timeout(1000, TimeUnit.MILLISECONDS)
+    timeout.cancel()
+    val start = now()
+    try {
+      lock.withLock {
+        timeout.awaitSignal(condition)
+      }
+      fail()
+    } catch (expected: InterruptedIOException) {
+      assertEquals("timeout", expected.message)
+    }
+    assertElapsed(1000.0, start)
+  }
+
+  @Test
+  fun canceledTimeoutDoesNotThrowWhenNotNotifiedOnTime() {
+    assumeNotWindows()
+    val timeout = Timeout()
+    timeout.timeout(1000, TimeUnit.MILLISECONDS)
+    timeout.cancelLater(500)
+
+    val start = now()
+    lock.withLock {
+      timeout.awaitSignal(condition) // Returns early but doesn't throw.
+    }
+    assertElapsed(1000.0, start)
+  }
+
+  @Test
+  @Synchronized
+  fun multipleCancelsAreIdempotent() {
+    val timeout = Timeout()
+    timeout.timeout(1000, TimeUnit.MILLISECONDS)
+    timeout.cancelLater(250)
+    timeout.cancelLater(500)
+    timeout.cancelLater(750)
+
+    val start = now()
+    lock.withLock {
+      timeout.awaitSignal(condition) // Returns early but doesn't throw.
+    }
+    assertElapsed(1000.0, start)
+  }
+
   /** Returns the nanotime in milliseconds as a double for measuring timeouts.  */
   private fun now(): Double {
     return System.nanoTime() / 1000000.0
@@ -166,6 +215,14 @@ class AwaitSignalTest {
    * -50..+450 milliseconds.
    */
   private fun assertElapsed(duration: Double, start: Double) {
-    Assert.assertEquals(duration, now() - start - 200.0, 250.0)
+    assertEquals(duration, now() - start - 200.0, 250.0)
+  }
+
+  private fun Timeout.cancelLater(delay: Long) {
+    executorService.schedule(
+      { cancel() },
+      delay,
+      TimeUnit.MILLISECONDS,
+    )
   }
 }