diff --git a/cmd/arcaflow/main.go b/cmd/arcaflow/main.go
index 967ebf90..b87ca800 100644
--- a/cmd/arcaflow/main.go
+++ b/cmd/arcaflow/main.go
@@ -6,6 +6,7 @@ import (
 	"flag"
 	"fmt"
 	"os"
+	"os/signal"
 	"path/filepath"
 	"strings"
 
@@ -164,13 +165,21 @@ Options:
 
 func runWorkflow(flow engine.WorkflowEngine, dirContext map[string][]byte, workflowFile string, logger log.Logger, inputData []byte) int {
 	ctx, cancel := context.WithCancel(context.Background())
-	defer cancel()
+	ctrlC := make(chan os.Signal, 4) // We expect up to three ctrl-C inputs. Plus one extra to buffer in case.
+	signal.Notify(ctrlC, os.Interrupt)
+
+	go handleOSInterrupt(ctrlC, cancel, logger)
+	defer func() {
+		close(ctrlC) // Ensure that the goroutine exits
+		cancel()
+	}()
 
 	workflow, err := flow.Parse(dirContext, workflowFile)
 	if err != nil {
 		logger.Errorf("Invalid workflow (%v)", err)
 		return ExitCodeInvalidData
 	}
+
 	outputID, outputData, outputError, err := workflow.Run(ctx, inputData)
 	if err != nil {
 		logger.Errorf("Workflow execution failed (%v)", err)
@@ -193,6 +202,28 @@ func runWorkflow(flow engine.WorkflowEngine, dirContext map[string][]byte, workf
 	return ExitCodeOK
 }
 
+func handleOSInterrupt(ctrlC chan os.Signal, cancel context.CancelFunc, logger log.Logger) {
+	_, ok := <-ctrlC
+	if !ok {
+		return
+	}
+	logger.Infof("Requesting graceful shutdown.")
+	cancel()
+
+	_, ok = <-ctrlC
+	if !ok {
+		return
+	}
+	logger.Warningf("Hit CTRL-C again to forcefully exit workflow without cleanup. You may need to manually delete pods or containers.")
+
+	_, ok = <-ctrlC
+	if !ok {
+		return
+	}
+	logger.Warningf("Force exiting. You may need to manually delete pods or containers.")
+	os.Exit(1)
+}
+
 func loadContext(dir string) (map[string][]byte, error) {
 	absDir, err := filepath.Abs(dir)
 	if err != nil {
diff --git a/cmd/run-plugin/run.go b/cmd/run-plugin/run.go
index f3a19138..7675b704 100644
--- a/cmd/run-plugin/run.go
+++ b/cmd/run-plugin/run.go
@@ -91,7 +91,7 @@ func main() {
 	if err != nil {
 		panic(err)
 	}
-	ctrlC := make(chan os.Signal, 1)
+	ctrlC := make(chan os.Signal, 1) // Buffer of one to properly buffer if the signal is sent early.
 	signal.Notify(ctrlC, os.Interrupt)
 
 	// Set up the signal channel to send cancel signal on ctrl-c
diff --git a/engine.go b/engine.go
index d82687a3..0411a9dc 100644
--- a/engine.go
+++ b/engine.go
@@ -62,7 +62,12 @@ type workflowEngine struct {
 	config       *config.Config
 }
 
-func (w workflowEngine) RunWorkflow(ctx context.Context, input []byte, workflowContext map[string][]byte, workflowFileName string) (outputID string, outputData any, outputError bool, err error) {
+func (w workflowEngine) RunWorkflow(
+	ctx context.Context,
+	input []byte,
+	workflowContext map[string][]byte,
+	workflowFileName string,
+) (outputID string, outputData any, outputError bool, err error) {
 	wf, err := w.Parse(workflowContext, workflowFileName)
 	if err != nil {
 		return "", nil, true, err
@@ -126,7 +131,10 @@ type engineWorkflow struct {
 	workflow workflow.ExecutableWorkflow
 }
 
-func (e engineWorkflow) Run(ctx context.Context, input []byte) (outputID string, outputData any, outputIsError bool, err error) {
+func (e engineWorkflow) Run(
+	ctx context.Context,
+	input []byte,
+) (outputID string, outputData any, outputIsError bool, err error) {
 	decodedInput, err := yaml.New().Parse(input)
 	if err != nil {
 		return "", nil, true, fmt.Errorf("failed to YAML decode input (%w)", err)
diff --git a/workflow/workflow_test.go b/workflow/workflow_test.go
index 330b7ed0..350cca7c 100644
--- a/workflow/workflow_test.go
+++ b/workflow/workflow_test.go
@@ -493,3 +493,65 @@ func TestMissingInputsWrongOutput(t *testing.T) {
 	assert.Error(t, err)
 	assert.Equals(t, outputID, "")
 }
+
+var fiveSecWaitWorkflowDefinition = `
+version: v0.2.0
+input:
+  root: RootObject
+  objects:
+    RootObject:
+      id: RootObject
+      properties: {}
+steps:
+  long_wait:
+    plugin:
+      src: "n/a"
+      deployment_type: "builtin"
+    step: wait
+    input:
+      wait_time_ms: 5000
+outputs:
+  success:
+    first_step_output: !expr $.steps.long_wait.outputs
+`
+
+func TestEarlyContextCancellation(t *testing.T) {
+	// For this test, a workflow runs two steps, where each step runs a wait step for 5s
+	// The second wait step waits for the first to succeed after which it runs
+	// Due to the wait for condition, the steps will execute serially
+	// The total execution time for this test function should be greater than 10seconds
+	// as each step runs for 5s and are run serially
+	// The test double deployer will be used for this test, as we
+	// need a deployer to test the plugin step provider.
+	logConfig := log.Config{
+		Level:       log.LevelInfo,
+		Destination: log.DestinationStdout,
+	}
+	logger := log.New(
+		logConfig,
+	)
+	cfg := &config.Config{
+		Log: logConfig,
+	}
+	stepRegistry := NewTestImplStepRegistry(logger, t)
+
+	executor := lang.Must2(workflow.NewExecutor(
+		logger,
+		cfg,
+		stepRegistry,
+	))
+	wf := lang.Must2(workflow.NewYAMLConverter(stepRegistry).FromYAML([]byte(fiveSecWaitWorkflowDefinition)))
+	preparedWorkflow := lang.Must2(executor.Prepare(wf, map[string][]byte{}))
+	// Cancel the context after 3 ms to simulate cancellation with ctrl-c.
+	ctx, cancel := context.WithTimeout(context.Background(), time.Millisecond*3)
+	startTime := time.Now() // Right before execute to not include pre-processing time.
+	//nolint:dogsled
+	_, _, _ = preparedWorkflow.Execute(ctx, map[string]any{})
+	cancel()
+
+	duration := time.Since(startTime)
+	t.Logf("Test execution time: %s", duration)
+	if duration >= 1000*time.Millisecond {
+		t.Fatalf("Test execution time is greater than 1000 milliseconds; Is the workflow properly cancelling?")
+	}
+}