diff --git a/await.go b/await.go
index 693da577..6366fc28 100644
--- a/await.go
+++ b/await.go
@@ -56,6 +56,9 @@ func NewPublicationAwaiter(ctx context.Context, readCheckpoint func(ctx context.
 type PublicationAwaiter struct {
 	c *sync.Cond
 
+	// Only used for testing coordination
+	preWaitSignaller chan struct{}
+
 	// size, checkpoint, and err keep track of the latest size and checkpoint
 	// (or error) seen by the poller.
 	size       uint64
@@ -83,17 +86,20 @@ func (a *PublicationAwaiter) Await(ctx context.Context, future IndexFuture) (Ind
 		span.AddEvent("Waiting for tree growth")
 		a.c.L.Lock()
 		defer a.c.L.Unlock()
+		if a.preWaitSignaller != nil {
+			a.preWaitSignaller <- struct{}{}
+		}
 		for (a.size <= i.Index && a.err == nil) && ctx.Err() == nil {
 			a.c.Wait()
 		}
-		// Ensure we propogate context done error, if any.
-		if err := ctx.Err(); err != nil {
-			a.err = err
-		} else {
-			span.AddEvent("Tree covers index")
+
+		// Make sure we report any errors that caused us to stop early
+		err = a.err
+		if err == nil {
+			err = ctx.Err()
 		}
 
-		return i, a.checkpoint, a.err
+		return i, a.checkpoint, err
 	})
 }
 
diff --git a/await_test.go b/await_test.go
index 89b62669..c077a99d 100644
--- a/await_test.go
+++ b/await_test.go
@@ -174,7 +174,7 @@ func TestAwait_multiClient(t *testing.T) {
 	testTimeout := 1 * time.Second
 	// Await will time out via this context, causing tests to fail
 	// if the integration condition is never reached.
-	ctx, cancel := context.WithTimeout(context.Background(), testTimeout)
+	ctx, cancel := context.WithTimeout(t.Context(), testTimeout)
 	defer cancel()
 
 	size := uint64(0)
@@ -204,8 +204,7 @@ func TestAwait_multiClient(t *testing.T) {
 			<-time.After(15 * time.Millisecond)
 			return Index{Index: index}, nil
 		}
-		wg.Add(1)
-		go func() {
+		wg.Go(func() {
 			i, cpRaw, err := awaiter.Await(ctx, future)
 			if err != nil {
 				t.Errorf("function for %d failed: %v", i.Index, err)
@@ -221,9 +220,77 @@ func TestAwait_multiClient(t *testing.T) {
 				t.Errorf("got cp size of %d for index %d", cp.Size, i.Index)
 			}
 
-			wg.Done()
-		}()
+		})
+	}
+	wg.Wait()
+}
+
+func TestAwait_contextCancel(t *testing.T) {
+	s, err := note.NewSigner("PRIVATE+KEY+example.com/log/testdata+33d7b496+AeymY/SZAX0jZcJ8enZ5FY1Dz+wTML2yWSkK+9DSF3eg")
+	if err != nil {
+		t.Fatal(err)
+	}
+
+	t.Parallel()
+	testTimeout := 2 * time.Second
+	// Await will time out via this context, causing tests to fail
+	// if the integration condition is never reached.
+	ctx, cancel := context.WithTimeout(t.Context(), testTimeout)
+	defer cancel()
+
+	var size atomic.Uint64
+	readCheckpoint := func(ctx context.Context) ([]byte, error) {
+		thisSize := size.Load()
+		hash := sha256.Sum256(fmt.Append(nil, thisSize))
+		cpRaw := log.Checkpoint{
+			Origin: "example.com/log/testdata",
+			Size:   thisSize,
+			Hash:   hash[:],
+		}.Marshal()
+		n, err := note.Sign(&note.Note{Text: string(cpRaw)}, s)
+		if err != nil {
+			return nil, fmt.Errorf("note.Sign: %w", err)
+		}
+		return n, nil
 	}
+	awaiter := NewPublicationAwaiter(ctx, readCheckpoint, 10*time.Millisecond)
+	awaiter.preWaitSignaller = make(chan struct{}, 2)
+
+	wg := sync.WaitGroup{}
+
+	// This one should succeed
+	wg.Go(func() {
+		future := func() (Index, error) {
+			return Index{Index: 50}, nil
+		}
+		_, _, err := awaiter.Await(ctx, future)
+		if err != nil {
+			t.Error(err)
+		}
+	})
+
+	timeoutSuccess := make(chan struct{})
+	// This one is expected to hit deadline exceeded
+	wg.Go(func() {
+		cctx, cancel := context.WithTimeout(ctx, 50*time.Millisecond)
+		defer cancel()
+		defer close(timeoutSuccess)
+		future := func() (Index, error) {
+			return Index{Index: 100}, nil
+		}
+		_, _, err := awaiter.Await(cctx, future)
+		if !errors.Is(err, context.DeadlineExceeded) {
+			t.Errorf("Expected context deadline exceeded, got %v", err)
+		}
+	})
+
+	// Block until both of the goroutines are waiting
+	<-awaiter.preWaitSignaller
+	<-awaiter.preWaitSignaller
+	// Then wait until the second one has timed out
+	<-timeoutSuccess
+	// And finally release the final one for success
+	size.Store(75)
 	wg.Wait()
 }