diff --git a/coderd/activitybump.go b/coderd/activitybump.go
new file mode 100644
index 0000000000000..fa90f7d275daf
--- /dev/null
+++ b/coderd/activitybump.go
@@ -0,0 +1,79 @@
+package coderd
+
+import (
+	"context"
+	"database/sql"
+	"errors"
+	"time"
+
+	"golang.org/x/xerrors"
+
+	"cdr.dev/slog"
+	"github.com/coder/coder/coderd/database"
+)
+
+// activityBumpWorkspace automatically bumps the workspace's auto-off timer
+// if it is set to expire soon.
+func activityBumpWorkspace(log slog.Logger, db database.Store, workspace database.Workspace) {
+	// We set a short timeout so if the app is under load, these
+	// low priority operations fail first.
+	ctx, cancel := context.WithTimeout(context.Background(), time.Second*15)
+	defer cancel()
+
+	err := db.InTx(func(s database.Store) error {
+		build, err := s.GetLatestWorkspaceBuildByWorkspaceID(ctx, workspace.ID)
+		if errors.Is(err, sql.ErrNoRows) {
+			return nil
+		} else if err != nil {
+			return xerrors.Errorf("get latest workspace build: %w", err)
+		}
+
+		job, err := s.GetProvisionerJobByID(ctx, build.JobID)
+		if err != nil {
+			return xerrors.Errorf("get provisioner job: %w", err)
+		}
+
+		if build.Transition != database.WorkspaceTransitionStart || !job.CompletedAt.Valid {
+			return nil
+		}
+
+		if build.Deadline.IsZero() {
+			// Workspace shutdown is manual
+			return nil
+		}
+
+		// We sent bumpThreshold slightly under bumpAmount to minimize DB writes.
+		const (
+			bumpAmount    = time.Hour
+			bumpThreshold = time.Hour - (time.Minute * 10)
+		)
+
+		if !build.Deadline.Before(time.Now().Add(bumpThreshold)) {
+			return nil
+		}
+
+		newDeadline := database.Now().Add(bumpAmount)
+
+		if err := s.UpdateWorkspaceBuildByID(ctx, database.UpdateWorkspaceBuildByIDParams{
+			ID:               build.ID,
+			UpdatedAt:        database.Now(),
+			ProvisionerState: build.ProvisionerState,
+			Deadline:         newDeadline,
+		}); err != nil {
+			return xerrors.Errorf("update workspace build: %w", err)
+		}
+		return nil
+	})
+	if err != nil {
+		log.Error(
+			ctx, "bump failed",
+			slog.Error(err),
+			slog.F("workspace_id", workspace.ID),
+		)
+	} else {
+		log.Debug(
+			ctx, "bumped deadline from activity",
+			slog.F("workspace_id", workspace.ID),
+		)
+	}
+}
diff --git a/coderd/activitybump_test.go b/coderd/activitybump_test.go
new file mode 100644
index 0000000000000..39c2f5fc6c5c8
--- /dev/null
+++ b/coderd/activitybump_test.go
@@ -0,0 +1,100 @@
+package coderd_test
+
+import (
+	"context"
+	"testing"
+	"time"
+
+	"github.com/stretchr/testify/require"
+
+	"cdr.dev/slog/sloggers/slogtest"
+
+	"github.com/coder/coder/coderd/coderdtest"
+	"github.com/coder/coder/coderd/database"
+	"github.com/coder/coder/codersdk"
+	"github.com/coder/coder/testutil"
+)
+
+func TestWorkspaceActivityBump(t *testing.T) {
+	t.Parallel()
+
+	ctx := context.Background()
+
+	setupActivityTest := func(t *testing.T) (client *codersdk.Client, workspace codersdk.Workspace, assertBumped func(want bool)) {
+		var ttlMillis int64 = 60 * 1000
+
+		client, _, workspace, _ = setupProxyTest(t, func(cwr *codersdk.CreateWorkspaceRequest) {
+			cwr.TTLMillis = &ttlMillis
+		})
+
+		// Sanity-check that deadline is near.
+		workspace, err := client.Workspace(ctx, workspace.ID)
+		require.NoError(t, err)
+		require.WithinDuration(t,
+			time.Now().Add(time.Duration(ttlMillis)*time.Millisecond),
+			workspace.LatestBuild.Deadline.Time, testutil.WaitShort,
+		)
+		firstDeadline := workspace.LatestBuild.Deadline.Time
+
+		_ = coderdtest.AwaitWorkspaceAgents(t, client, workspace.LatestBuild.ID)
+
+		return client, workspace, func(want bool) {
+			if !want {
+				// It is difficult to test the absence of a call in a non-racey
+				// way. In general, it is difficult for the API to generate
+				// false positive activity since Agent networking event
+				// is required. The Activity Bump behavior is also coupled with
+				// Last Used, so it would be obvious to the user if we
+				// are falsely recognizing activity.
+				time.Sleep(testutil.IntervalMedium)
+				workspace, err = client.Workspace(ctx, workspace.ID)
+				require.NoError(t, err)
+				require.Equal(t, workspace.LatestBuild.Deadline.Time, firstDeadline)
+				return
+			}
+
+			// The Deadline bump occurs asynchronously.
+			require.Eventuallyf(t,
+				func() bool {
+					workspace, err = client.Workspace(ctx, workspace.ID)
+					require.NoError(t, err)
+					return workspace.LatestBuild.Deadline.Time != firstDeadline
+				},
+				testutil.WaitShort, testutil.IntervalFast,
+				"deadline %v never updated", firstDeadline,
+			)
+
+			require.WithinDuration(t, database.Now().Add(time.Hour), workspace.LatestBuild.Deadline.Time, time.Second)
+		}
+	}
+
+	t.Run("Dial", func(t *testing.T) {
+		t.Parallel()
+
+		client, workspace, assertBumped := setupActivityTest(t)
+
+		resources := coderdtest.AwaitWorkspaceAgents(t, client, workspace.LatestBuild.ID)
+		conn, err := client.DialWorkspaceAgentTailnet(ctx, slogtest.Make(t, nil), resources[0].Agents[0].ID)
+		require.NoError(t, err)
+		defer conn.Close()
+
+		sshConn, err := conn.SSHClient()
+		require.NoError(t, err)
+		_ = sshConn.Close()
+
+		assertBumped(true)
+	})
+
+	t.Run("NoBump", func(t *testing.T) {
+		t.Parallel()
+
+		client, workspace, assertBumped := setupActivityTest(t)
+
+		// Benign operations like retrieving resources must not
+		// bump the deadline.
+		_, err := client.WorkspaceResourcesByBuild(ctx, workspace.LatestBuild.ID)
+		require.NoError(t, err)
+
+		assertBumped(false)
+	})
+}
diff --git a/coderd/workspaceagents.go b/coderd/workspaceagents.go
index 57c90c5b84479..219fbb78b7d00 100644
--- a/coderd/workspaceagents.go
+++ b/coderd/workspaceagents.go
@@ -616,6 +616,8 @@ func (api *API) workspaceAgentReportStats(rw http.ResponseWriter, r *http.Reques
 		)
 
 		if updateDB {
+			go activityBumpWorkspace(api.Logger.Named("activity_bump"), api.Database, workspace)
+
 			lastReport = rep
 
 			_, err = api.Database.InsertAgentStat(ctx, database.InsertAgentStatParams{
diff --git a/coderd/workspaceapps_test.go b/coderd/workspaceapps_test.go
index 831b3761693df..164ceb2b15de6 100644
--- a/coderd/workspaceapps_test.go
+++ b/coderd/workspaceapps_test.go
@@ -36,7 +36,7 @@ const (
 // setupProxyTest creates a workspace with an agent and some apps. It returns a
 // codersdk client, the workspace, and the port number the test listener is
 // running on.
-func setupProxyTest(t *testing.T) (*codersdk.Client, uuid.UUID, codersdk.Workspace, uint16) {
+func setupProxyTest(t *testing.T, workspaceMutators ...func(*codersdk.CreateWorkspaceRequest)) (*codersdk.Client, uuid.UUID, codersdk.Workspace, uint16) {
 	// #nosec
 	ln, err := net.Listen("tcp", ":0")
 	require.NoError(t, err)
@@ -58,7 +58,9 @@ func setupProxyTest(t *testing.T) (*codersdk.Client, uuid.UUID, codersdk.Workspa
 	require.True(t, ok)
 
 	client := coderdtest.New(t, &coderdtest.Options{
-		IncludeProvisionerDaemon: true,
+		IncludeProvisionerDaemon:    true,
+		AgentStatsRefreshInterval:   time.Millisecond * 100,
+		MetricsCacheRefreshInterval: time.Millisecond * 100,
 	})
 	user := coderdtest.CreateFirstUser(t, client)
 	authToken := uuid.NewString()
@@ -95,7 +97,7 @@ func setupProxyTest(t *testing.T) (*codersdk.Client, uuid.UUID, codersdk.Workspa
 	})
 	template := coderdtest.CreateTemplate(t, client, user.OrganizationID, version.ID)
 	coderdtest.AwaitTemplateVersionJob(t, client, version.ID)
-	workspace := coderdtest.CreateWorkspace(t, client, user.OrganizationID, template.ID)
+	workspace := coderdtest.CreateWorkspace(t, client, user.OrganizationID, template.ID, workspaceMutators...)
 	coderdtest.AwaitWorkspaceBuildJob(t, client, workspace.LatestBuild.ID)
 
 	agentClient := codersdk.New(client.URL)
@@ -104,6 +106,7 @@ func setupProxyTest(t *testing.T) (*codersdk.Client, uuid.UUID, codersdk.Workspa
 		FetchMetadata:     agentClient.WorkspaceAgentMetadata,
 		CoordinatorDialer: agentClient.ListenWorkspaceAgentTailnet,
 		Logger:            slogtest.Make(t, nil).Named("agent"),
+		StatsReporter:     agentClient.AgentReportStats,
 	})
 	t.Cleanup(func() {
 		_ = agentCloser.Close()
diff --git a/codersdk/workspaceagents.go b/codersdk/workspaceagents.go
index 2117de03c6ce3..bf1f58eceafac 100644
--- a/codersdk/workspaceagents.go
+++ b/codersdk/workspaceagents.go
@@ -281,12 +281,10 @@ func (c *Client) DialWorkspaceAgentTailnet(ctx context.Context, logger slog.Logg
 				CompressionMode: websocket.CompressionDisabled,
 			})
 			if errors.Is(err, context.Canceled) {
-				_ = ws.Close(websocket.StatusAbnormalClosure, "")
 				return
 			}
 			if err != nil {
 				logger.Debug(ctx, "failed to dial", slog.Error(err))
-				_ = ws.Close(websocket.StatusAbnormalClosure, "")
 				continue
 			}
 			sendNode, errChan := tailnet.ServeCoordinator(websocket.NetConn(ctx, ws, websocket.MessageBinary), func(node []*tailnet.Node) error {
diff --git a/site/src/components/WorkspaceScheduleForm/WorkspaceScheduleForm.tsx b/site/src/components/WorkspaceScheduleForm/WorkspaceScheduleForm.tsx
index 1b53583ed141c..49f9aec931975 100644
--- a/site/src/components/WorkspaceScheduleForm/WorkspaceScheduleForm.tsx
+++ b/site/src/components/WorkspaceScheduleForm/WorkspaceScheduleForm.tsx
@@ -55,7 +55,8 @@ export const Language = {
   timezoneLabel: "Timezone",
   ttlLabel: "Time until shutdown (hours)",
   ttlCausesShutdownHelperText: "Your workspace will shut down",
-  ttlCausesShutdownAfterStart: "after its next start",
+  ttlCausesShutdownAfterStart:
+    "after its next start. We delay shutdown by an hour whenever we detect activity",
   ttlCausesNoShutdownHelperText: "Your workspace will not automatically shut down.",
   formTitle: "Workspace schedule",
   startSection: "Start",