diff --git a/cli/agent.go b/cli/agent.go
index af54bfc969..b900db48d0 100644
--- a/cli/agent.go
+++ b/cli/agent.go
@@ -125,7 +125,7 @@ func (r *RootCmd) workspaceAgent() *clibase.Cmd {
 				args := append(os.Args, "--no-reap")
 				err := reaper.ForkReap(
 					reaper.WithExecArgs(args...),
-					reaper.WithCatchSignals(InterruptSignals...),
+					reaper.WithCatchSignals(StopSignals...),
 				)
 				if err != nil {
 					logger.Error(ctx, "agent process reaper unable to fork", slog.Error(err))
@@ -144,7 +144,7 @@ func (r *RootCmd) workspaceAgent() *clibase.Cmd {
 			// Note that we don't want to handle these signals in the
 			// process that runs as PID 1, that's why we do this after
 			// the reaper forked.
-			ctx, stopNotify := inv.SignalNotifyContext(ctx, InterruptSignals...)
+			ctx, stopNotify := inv.SignalNotifyContext(ctx, StopSignals...)
 			defer stopNotify()
 
 			// DumpHandler does signal handling, so we call it after the
diff --git a/cli/exp_scaletest.go b/cli/exp_scaletest.go
index fc8f503f3a..fe93fe26cd 100644
--- a/cli/exp_scaletest.go
+++ b/cli/exp_scaletest.go
@@ -890,7 +890,7 @@ func (r *RootCmd) scaletestWorkspaceTraffic() *clibase.Cmd {
 		Handler: func(inv *clibase.Invocation) (err error) {
 			ctx := inv.Context()
 
-			notifyCtx, stop := signal.NotifyContext(ctx, InterruptSignals...) // Checked later.
+			notifyCtx, stop := signal.NotifyContext(ctx, StopSignals...) // Checked later.
 			defer stop()
 			ctx = notifyCtx
 
diff --git a/cli/externalauth.go b/cli/externalauth.go
index 675d795491..52b897b64b 100644
--- a/cli/externalauth.go
+++ b/cli/externalauth.go
@@ -65,7 +65,7 @@ fi
 		Handler: func(inv *clibase.Invocation) error {
 			ctx := inv.Context()
 
-			ctx, stop := inv.SignalNotifyContext(ctx, InterruptSignals...)
+			ctx, stop := inv.SignalNotifyContext(ctx, StopSignals...)
 			defer stop()
 
 			client, err := r.createAgentClient()
diff --git a/cli/gitaskpass.go b/cli/gitaskpass.go
index ddfd05af9d..30e82ab90a 100644
--- a/cli/gitaskpass.go
+++ b/cli/gitaskpass.go
@@ -25,7 +25,7 @@ func (r *RootCmd) gitAskpass() *clibase.Cmd {
 		Handler: func(inv *clibase.Invocation) error {
 			ctx := inv.Context()
 
-			ctx, stop := inv.SignalNotifyContext(ctx, InterruptSignals...)
+			ctx, stop := inv.SignalNotifyContext(ctx, StopSignals...)
 			defer stop()
 
 			user, host, err := gitauth.ParseAskpass(inv.Args[0])
diff --git a/cli/gitssh.go b/cli/gitssh.go
index b627b3911b..479ec094f0 100644
--- a/cli/gitssh.go
+++ b/cli/gitssh.go
@@ -29,7 +29,7 @@ func (r *RootCmd) gitssh() *clibase.Cmd {
 
 			// Catch interrupt signals to ensure the temporary private
 			// key file is cleaned up on most cases.
-			ctx, stop := inv.SignalNotifyContext(ctx, InterruptSignals...)
+			ctx, stop := inv.SignalNotifyContext(ctx, StopSignals...)
 			defer stop()
 
 			// Early check so errors are reported immediately.
diff --git a/cli/server.go b/cli/server.go
index e02a891022..937f290aff 100644
--- a/cli/server.go
+++ b/cli/server.go
@@ -337,7 +337,7 @@ func (r *RootCmd) Server(newAPI func(context.Context, *coderd.Options) (*coderd.
 
 			// Register signals early on so that graceful shutdown can't
 			// be interrupted by additional signals. Note that we avoid
-			// shadowing cancel() (from above) here because notifyStop()
+			// shadowing cancel() (from above) here because stopCancel()
 			// restores default behavior for the signals. This protects
 			// the shutdown sequence from abruptly terminating things
 			// like: database migrations, provisioner work, workspace
@@ -345,8 +345,10 @@ func (r *RootCmd) Server(newAPI func(context.Context, *coderd.Options) (*coderd.
 			//
 			// To get out of a graceful shutdown, the user can send
 			// SIGQUIT with ctrl+\ or SIGKILL with `kill -9`.
-			notifyCtx, notifyStop := inv.SignalNotifyContext(ctx, InterruptSignals...)
-			defer notifyStop()
+			stopCtx, stopCancel := signalNotifyContext(ctx, inv, StopSignalsNoInterrupt...)
+			defer stopCancel()
+			interruptCtx, interruptCancel := signalNotifyContext(ctx, inv, InterruptSignals...)
+			defer interruptCancel()
 
 			cacheDir := vals.CacheDir.String()
 			err = os.MkdirAll(cacheDir, 0o700)
@@ -1028,13 +1030,18 @@ func (r *RootCmd) Server(newAPI func(context.Context, *coderd.Options) (*coderd.
 			hangDetector.Start()
 			defer hangDetector.Close()
 
+			waitForProvisionerJobs := false
 			// Currently there is no way to ask the server to shut
 			// itself down, so any exit signal will result in a non-zero
 			// exit of the server.
 			var exitErr error
 			select {
-			case <-notifyCtx.Done():
-				exitErr = notifyCtx.Err()
+			case <-stopCtx.Done():
+				exitErr = stopCtx.Err()
+				waitForProvisionerJobs = true
+				_, _ = io.WriteString(inv.Stdout, cliui.Bold("Stop caught, waiting for provisioner jobs to complete and gracefully exiting. Use ctrl+\\ to force quit"))
+			case <-interruptCtx.Done():
+				exitErr = interruptCtx.Err()
 				_, _ = io.WriteString(inv.Stdout, cliui.Bold("Interrupt caught, gracefully exiting. Use ctrl+\\ to force quit"))
 			case <-tunnelDone:
 				exitErr = xerrors.New("dev tunnel closed unexpectedly")
@@ -1082,7 +1089,16 @@ func (r *RootCmd) Server(newAPI func(context.Context, *coderd.Options) (*coderd.
 					defer wg.Done()
 
 					r.Verbosef(inv, "Shutting down provisioner daemon %d...", id)
-					err := shutdownWithTimeout(provisionerDaemon.Shutdown, 5*time.Second)
+					timeout := 5 * time.Second
+					if waitForProvisionerJobs {
+						// It can last for a long time...
+						timeout = 30 * time.Minute
+					}
+
+					err := shutdownWithTimeout(func(ctx context.Context) error {
+						// We only want to cancel active jobs if we aren't exiting gracefully.
+						return provisionerDaemon.Shutdown(ctx, !waitForProvisionerJobs)
+					}, timeout)
 					if err != nil {
 						cliui.Errorf(inv.Stderr, "Failed to shut down provisioner daemon %d: %s\n", id, err)
 						return
@@ -2512,3 +2528,12 @@ func escapePostgresURLUserInfo(v string) (string, error) {
 
 	return v, nil
 }
+
+func signalNotifyContext(ctx context.Context, inv *clibase.Invocation, sig ...os.Signal) (context.Context, context.CancelFunc) {
+	// On Windows, some of our signal functions lack support.
+	// If we pass in no signals, we should just return the context as-is.
+	if len(sig) == 0 {
+		return context.WithCancel(ctx)
+	}
+	return inv.SignalNotifyContext(ctx, sig...)
+}
diff --git a/cli/server_createadminuser.go b/cli/server_createadminuser.go
index 7491afac3c..43f78ea784 100644
--- a/cli/server_createadminuser.go
+++ b/cli/server_createadminuser.go
@@ -47,7 +47,7 @@ func (r *RootCmd) newCreateAdminUserCommand() *clibase.Cmd {
 				logger = logger.Leveled(slog.LevelDebug)
 			}
 
-			ctx, cancel := inv.SignalNotifyContext(ctx, InterruptSignals...)
+			ctx, cancel := inv.SignalNotifyContext(ctx, StopSignals...)
 			defer cancel()
 
 			if newUserDBURL == "" {
diff --git a/cli/server_test.go b/cli/server_test.go
index 9699e8a48e..4ce4d2b5f5 100644
--- a/cli/server_test.go
+++ b/cli/server_test.go
@@ -21,6 +21,7 @@ import (
 	"net/url"
 	"os"
 	"path/filepath"
+	"reflect"
 	"runtime"
 	"strconv"
 	"strings"
@@ -1605,7 +1606,7 @@ func TestServer_Production(t *testing.T) {
 }
 
 //nolint:tparallel,paralleltest // This test cannot be run in parallel due to signal handling.
-func TestServer_Shutdown(t *testing.T) {
+func TestServer_InterruptShutdown(t *testing.T) {
 	t.Skip("This test issues an interrupt signal which will propagate to the test runner.")
 
 	if runtime.GOOS == "windows" {
@@ -1638,6 +1639,46 @@ func TestServer_Shutdown(t *testing.T) {
 	require.NoError(t, err)
 }
 
+func TestServer_GracefulShutdown(t *testing.T) {
+	t.Parallel()
+	if runtime.GOOS == "windows" {
+		// Sending interrupt signal isn't supported on Windows!
+		t.SkipNow()
+	}
+	ctx, cancelFunc := context.WithCancel(context.Background())
+	defer cancelFunc()
+
+	root, cfg := clitest.New(t,
+		"server",
+		"--in-memory",
+		"--http-address", ":0",
+		"--access-url", "http://example.com",
+		"--provisioner-daemons", "1",
+		"--cache-dir", t.TempDir(),
+	)
+	var stopFunc context.CancelFunc
+	root = root.WithTestSignalNotifyContext(t, func(parent context.Context, signals ...os.Signal) (context.Context, context.CancelFunc) {
+		if !reflect.DeepEqual(cli.StopSignalsNoInterrupt, signals) {
+			return context.WithCancel(ctx)
+		}
+		var ctx context.Context
+		ctx, stopFunc = context.WithCancel(parent)
+		return ctx, stopFunc
+	})
+	serverErr := make(chan error, 1)
+	pty := ptytest.New(t).Attach(root)
+	go func() {
+		serverErr <- root.WithContext(ctx).Run()
+	}()
+	_ = waitAccessURL(t, cfg)
+	// It's fair to assume `stopFunc` isn't nil here, because the server
+	// has started and access URL is propagated.
+	stopFunc()
+	pty.ExpectMatch("waiting for provisioner jobs to complete")
+	err := <-serverErr
+	require.NoError(t, err)
+}
+
 func BenchmarkServerHelp(b *testing.B) {
 	// server --help is a good proxy for measuring the
 	// constant overhead of each command.
diff --git a/cli/signal_unix.go b/cli/signal_unix.go
index 05d619c023..9cb6f3f899 100644
--- a/cli/signal_unix.go
+++ b/cli/signal_unix.go
@@ -7,8 +7,23 @@ import (
 	"syscall"
 )
 
-var InterruptSignals = []os.Signal{
+// StopSignals is the list of signals that are used for handling
+// shutdown behavior.
+var StopSignals = []os.Signal{
 	os.Interrupt,
 	syscall.SIGTERM,
 	syscall.SIGHUP,
 }
+
+// StopSignals is the list of signals that are used for handling
+// graceful shutdown behavior.
+var StopSignalsNoInterrupt = []os.Signal{
+	syscall.SIGTERM,
+	syscall.SIGHUP,
+}
+
+// InterruptSignals is the list of signals that are used for handling
+// immediate shutdown behavior.
+var InterruptSignals = []os.Signal{
+	os.Interrupt,
+}
diff --git a/cli/signal_windows.go b/cli/signal_windows.go
index 3624415a64..8d9b8518e6 100644
--- a/cli/signal_windows.go
+++ b/cli/signal_windows.go
@@ -6,4 +6,12 @@ import (
 	"os"
 )
 
-var InterruptSignals = []os.Signal{os.Interrupt}
+var StopSignals = []os.Signal{
+	os.Interrupt,
+}
+
+var StopSignalsNoInterrupt = []os.Signal{}
+
+var InterruptSignals = []os.Signal{
+	os.Interrupt,
+}
diff --git a/cli/ssh.go b/cli/ssh.go
index 21437ee6ae..023c5307da 100644
--- a/cli/ssh.go
+++ b/cli/ssh.go
@@ -73,7 +73,7 @@ func (r *RootCmd) ssh() *clibase.Cmd {
 			// session can persist for up to 72 hours, since we set a long
 			// timeout on the Agent side of the connection.  In particular,
 			// OpenSSH sends SIGHUP to terminate a proxy command.
-			ctx, stop := inv.SignalNotifyContext(inv.Context(), InterruptSignals...)
+			ctx, stop := inv.SignalNotifyContext(inv.Context(), StopSignals...)
 			defer stop()
 			ctx, cancel := context.WithCancel(ctx)
 			defer cancel()
diff --git a/cli/templatepull_test.go b/cli/templatepull_test.go
index ec7beb6196..1b1d51b0cc 100644
--- a/cli/templatepull_test.go
+++ b/cli/templatepull_test.go
@@ -328,7 +328,7 @@ func TestTemplatePull_ToDir(t *testing.T) {
 
 			require.NoError(t, inv.Run())
 
-			// Validate behaviour of choosing template name in the absence of an output path argument.
+			// Validate behavior of choosing template name in the absence of an output path argument.
 			destPath := actualDest
 			if destPath == "" {
 				destPath = template.Name
diff --git a/coderd/coderdtest/coderdtest.go b/coderd/coderdtest/coderdtest.go
index 85d92a5ef6..4d315c3e2b 100644
--- a/coderd/coderdtest/coderdtest.go
+++ b/coderd/coderdtest/coderdtest.go
@@ -498,7 +498,7 @@ func (c *provisionerdCloser) Close() error {
 	c.closed = true
 	ctx, cancel := context.WithTimeout(context.Background(), testutil.WaitShort)
 	defer cancel()
-	shutdownErr := c.d.Shutdown(ctx)
+	shutdownErr := c.d.Shutdown(ctx, true)
 	closeErr := c.d.Close()
 	if shutdownErr != nil {
 		return shutdownErr
diff --git a/enterprise/cli/provisionerdaemons.go b/enterprise/cli/provisionerdaemons.go
index 5943758a7d..6f356e541d 100644
--- a/enterprise/cli/provisionerdaemons.go
+++ b/enterprise/cli/provisionerdaemons.go
@@ -88,8 +88,10 @@ func (r *RootCmd) provisionerDaemonStart() *clibase.Cmd {
 			ctx, cancel := context.WithCancel(inv.Context())
 			defer cancel()
 
-			notifyCtx, notifyStop := inv.SignalNotifyContext(ctx, agpl.InterruptSignals...)
-			defer notifyStop()
+			stopCtx, stopCancel := inv.SignalNotifyContext(ctx, agpl.StopSignalsNoInterrupt...)
+			defer stopCancel()
+			interruptCtx, interruptCancel := inv.SignalNotifyContext(ctx, agpl.InterruptSignals...)
+			defer interruptCancel()
 
 			tags, err := agpl.ParseProvisionerTags(rawTags)
 			if err != nil {
@@ -212,10 +214,17 @@ func (r *RootCmd) provisionerDaemonStart() *clibase.Cmd {
 				Metrics:        metrics,
 			})
 
+			waitForProvisionerJobs := false
 			var exitErr error
 			select {
-			case <-notifyCtx.Done():
-				exitErr = notifyCtx.Err()
+			case <-stopCtx.Done():
+				exitErr = stopCtx.Err()
+				_, _ = fmt.Fprintln(inv.Stdout, cliui.Bold(
+					"Stop caught, waiting for provisioner jobs to complete and gracefully exiting. Use ctrl+\\ to force quit",
+				))
+				waitForProvisionerJobs = true
+			case <-interruptCtx.Done():
+				exitErr = interruptCtx.Err()
 				_, _ = fmt.Fprintln(inv.Stdout, cliui.Bold(
 					"Interrupt caught, gracefully exiting. Use ctrl+\\ to force quit",
 				))
@@ -225,7 +234,7 @@ func (r *RootCmd) provisionerDaemonStart() *clibase.Cmd {
 				cliui.Errorf(inv.Stderr, "Unexpected error, shutting down server: %s\n", exitErr)
 			}
 
-			err = srv.Shutdown(ctx)
+			err = srv.Shutdown(ctx, waitForProvisionerJobs)
 			if err != nil {
 				return xerrors.Errorf("shutdown: %w", err)
 			}
diff --git a/enterprise/cli/proxyserver.go b/enterprise/cli/proxyserver.go
index a31d2fe829..68ec04b966 100644
--- a/enterprise/cli/proxyserver.go
+++ b/enterprise/cli/proxyserver.go
@@ -142,7 +142,7 @@ func (r *RootCmd) proxyServer() *clibase.Cmd {
 			//
 			// To get out of a graceful shutdown, the user can send
 			// SIGQUIT with ctrl+\ or SIGKILL with `kill -9`.
-			notifyCtx, notifyStop := inv.SignalNotifyContext(ctx, cli.InterruptSignals...)
+			notifyCtx, notifyStop := inv.SignalNotifyContext(ctx, cli.StopSignals...)
 			defer notifyStop()
 
 			// Clean up idle connections at the end, e.g.
diff --git a/enterprise/coderd/provisionerdaemons_test.go b/enterprise/coderd/provisionerdaemons_test.go
index caa65c8850..c62a91593d 100644
--- a/enterprise/coderd/provisionerdaemons_test.go
+++ b/enterprise/coderd/provisionerdaemons_test.go
@@ -441,7 +441,7 @@ func TestProvisionerDaemonServe(t *testing.T) {
 		build := coderdtest.AwaitWorkspaceBuildJobCompleted(t, client, workspace.LatestBuild.ID)
 		require.Equal(t, codersdk.WorkspaceStatusRunning, build.Status)
 
-		err = pd.Shutdown(ctx)
+		err = pd.Shutdown(ctx, false)
 		require.NoError(t, err)
 		err = terraformServer.Close()
 		require.NoError(t, err)
diff --git a/provisionerd/provisionerd.go b/provisionerd/provisionerd.go
index 52414db4af..3e49648700 100644
--- a/provisionerd/provisionerd.go
+++ b/provisionerd/provisionerd.go
@@ -474,15 +474,18 @@ func (p *Server) isClosed() bool {
 	}
 }
 
-// Shutdown triggers a graceful exit of each registered provisioner.
-func (p *Server) Shutdown(ctx context.Context) error {
+// Shutdown gracefully exists with the option to cancel the active job.
+// If false, it will wait for the job to complete.
+//
+//nolint:revive
+func (p *Server) Shutdown(ctx context.Context, cancelActiveJob bool) error {
 	p.mutex.Lock()
 	p.opts.Logger.Info(ctx, "attempting graceful shutdown")
 	if !p.shuttingDownB {
 		close(p.shuttingDownCh)
 		p.shuttingDownB = true
 	}
-	if p.activeJob != nil {
+	if cancelActiveJob && p.activeJob != nil {
 		p.activeJob.Cancel()
 	}
 	p.mutex.Unlock()
diff --git a/provisionerd/provisionerd_test.go b/provisionerd/provisionerd_test.go
index a04196e6b4..2031fa6c39 100644
--- a/provisionerd/provisionerd_test.go
+++ b/provisionerd/provisionerd_test.go
@@ -671,7 +671,7 @@ func TestProvisionerd(t *testing.T) {
 			}),
 		})
 		require.Condition(t, closedWithin(updateChan, testutil.WaitShort))
-		err := server.Shutdown(context.Background())
+		err := server.Shutdown(context.Background(), true)
 		require.NoError(t, err)
 		require.Condition(t, closedWithin(completeChan, testutil.WaitShort))
 		require.NoError(t, server.Close())
@@ -762,7 +762,7 @@ func TestProvisionerd(t *testing.T) {
 		require.Condition(t, closedWithin(completeChan, testutil.WaitShort))
 		ctx, cancel := context.WithTimeout(context.Background(), testutil.WaitShort)
 		defer cancel()
-		require.NoError(t, server.Shutdown(ctx))
+		require.NoError(t, server.Shutdown(ctx, true))
 		require.NoError(t, server.Close())
 	})
 
@@ -853,7 +853,7 @@ func TestProvisionerd(t *testing.T) {
 		require.Condition(t, closedWithin(completeChan, testutil.WaitShort))
 		ctx, cancel := context.WithTimeout(context.Background(), testutil.WaitShort)
 		defer cancel()
-		require.NoError(t, server.Shutdown(ctx))
+		require.NoError(t, server.Shutdown(ctx, true))
 		require.NoError(t, server.Close())
 	})
 
@@ -944,7 +944,7 @@ func TestProvisionerd(t *testing.T) {
 		t.Log("completeChan closed")
 		ctx, cancel := context.WithTimeout(context.Background(), testutil.WaitShort)
 		defer cancel()
-		require.NoError(t, server.Shutdown(ctx))
+		require.NoError(t, server.Shutdown(ctx, true))
 		require.NoError(t, server.Close())
 	})
 
@@ -1039,7 +1039,7 @@ func TestProvisionerd(t *testing.T) {
 		require.Condition(t, closedWithin(completeChan, testutil.WaitShort))
 		ctx, cancel := context.WithTimeout(context.Background(), testutil.WaitShort)
 		defer cancel()
-		require.NoError(t, server.Shutdown(ctx))
+		require.NoError(t, server.Shutdown(ctx, true))
 		require.NoError(t, server.Close())
 		assert.Equal(t, ops[len(ops)-1], "CompleteJob")
 		assert.Contains(t, ops[0:len(ops)-1], "Log: Cleaning Up | ")
@@ -1076,7 +1076,7 @@ func createProvisionerd(t *testing.T, dialer provisionerd.Dialer, connector prov
 	t.Cleanup(func() {
 		ctx, cancel := context.WithTimeout(context.Background(), testutil.WaitShort)
 		defer cancel()
-		_ = server.Shutdown(ctx)
+		_ = server.Shutdown(ctx, true)
 		_ = server.Close()
 	})
 	return server