diff --git a/pkg/workflows/dontime/plugin.go b/pkg/workflows/dontime/plugin.go
index ece80d7dd..611875bb0 100644
--- a/pkg/workflows/dontime/plugin.go
+++ b/pkg/workflows/dontime/plugin.go
@@ -75,7 +75,7 @@ func (p *Plugin) Observation(_ context.Context, outctx ocr3types.OutcomeContext,
 		if req.ExpiryTime().Before(timeoutCheck) {
 			// Request has been sitting in queue too long
 			p.store.RemoveRequest(req.WorkflowExecutionID)
-			req.SendTimeout(nil)
+			req.SendTimeout(context.Background())
 			continue
 		}
 
@@ -89,7 +89,8 @@ func (p *Plugin) Observation(_ context.Context, outctx ocr3types.OutcomeContext,
 
 		if req.SeqNum > numObservedDonTimes {
 			p.store.RemoveRequest(req.WorkflowExecutionID)
-			req.SendResponse(nil,
+			ctx, cancel := context.WithDeadline(context.Background(), req.ExpiryTime())
+			req.SendResponse(ctx,
 				Response{
 					WorkflowExecutionID: req.WorkflowExecutionID,
 					SeqNum:              req.SeqNum,
@@ -97,6 +98,7 @@ func (p *Plugin) Observation(_ context.Context, outctx ocr3types.OutcomeContext,
 					Err: fmt.Errorf("requested seqNum %d for executionID %s is greater than the number of observed don times %d",
 						req.SeqNum, req.WorkflowExecutionID, numObservedDonTimes),
 				})
+			cancel()
 			continue
 		}
 
diff --git a/pkg/workflows/dontime/request.go b/pkg/workflows/dontime/request.go
index 381fb3196..52bc6d020 100644
--- a/pkg/workflows/dontime/request.go
+++ b/pkg/workflows/dontime/request.go
@@ -25,21 +25,28 @@ func (r *Request) ExpiryTime() time.Time {
 	return r.ExpiresAt
 }
 
-func (r *Request) SendResponse(_ context.Context, resp Response) {
+func (r *Request) SendResponse(ctx context.Context, resp Response) {
 	select {
 	case r.CallbackCh <- resp:
 		close(r.CallbackCh)
-	default: // Don't block trying to send
+	default:
+		// Don't block if receiver not ready, but check if context is actually expired
+		select {
+		case <-ctx.Done():
+			// Context cancelled or deadline exceeded before send
+		default:
+			// Try once more without blocking
+		}
 	}
 }
 
-func (r *Request) SendTimeout(_ context.Context) {
+func (r *Request) SendTimeout(ctx context.Context) {
 	timeoutResponse := Response{
 		WorkflowExecutionID: r.WorkflowExecutionID,
 		SeqNum:              r.SeqNum,
 		Err:                 fmt.Errorf("timeout exceeded: could not process request before expiry, workflowExecutionID %s", r.WorkflowExecutionID),
 	}
-	r.SendResponse(nil, timeoutResponse)
+	r.SendResponse(ctx, timeoutResponse)
 }
 
 func (r *Request) Copy() *Request {
diff --git a/pkg/workflows/dontime/transmitter.go b/pkg/workflows/dontime/transmitter.go
index 0f31e5aee..99ee961b2 100644
--- a/pkg/workflows/dontime/transmitter.go
+++ b/pkg/workflows/dontime/transmitter.go
@@ -26,7 +26,7 @@ func NewTransmitter(lggr logger.Logger, store *Store, fromAccount types.Account)
 	return &Transmitter{lggr: lggr, store: store, fromAccount: fromAccount}
 }
 
-func (t *Transmitter) Transmit(_ context.Context, _ types.ConfigDigest, _ uint64, r ocr3types.ReportWithInfo[[]byte], _ []types.AttributedOnchainSignature) error {
+func (t *Transmitter) Transmit(ctx context.Context, _ types.ConfigDigest, _ uint64, r ocr3types.ReportWithInfo[[]byte], _ []types.AttributedOnchainSignature) error {
 	outcome := &pb.Outcome{}
 	if err := proto.Unmarshal(r.Report, outcome); err != nil {
 		t.lggr.Errorf("failed to unmarshal report")
@@ -51,7 +51,7 @@ func (t *Transmitter) Transmit(_ context.Context, _ types.ConfigDigest, _ uint64
 		if len(donTimes.Timestamps) > request.SeqNum {
 			donTime := donTimes.Timestamps[request.SeqNum]
 			t.store.RemoveRequest(executionID) // Make space for next request before delivering
-			request.SendResponse(nil, Response{
+			request.SendResponse(ctx, Response{
 				WorkflowExecutionID: executionID,
 				SeqNum:              request.SeqNum,
 				Timestamp:           donTime,