diff --git a/coderd/database/pubsub/pubsub_test.go b/coderd/database/pubsub/pubsub_test.go
index 1ee2801bd4..066b9ce59a 100644
--- a/coderd/database/pubsub/pubsub_test.go
+++ b/coderd/database/pubsub/pubsub_test.go
@@ -151,7 +151,10 @@ func TestPGPubsubDriver(t *testing.T) {
 	gotChan := make(chan struct{}, 1)
 	defer close(gotChan)
 	subCancel, err := subber.Subscribe("test", func(_ context.Context, _ []byte) {
-		gotChan <- struct{}{}
+		select {
+		case gotChan <- struct{}{}:
+		default:
+		}
 	})
 	require.NoError(t, err)
 	defer subCancel()
@@ -174,14 +177,27 @@ func TestPGPubsubDriver(t *testing.T) {
 
 	// wait for the reconnect
 	_ = testutil.TryReceive(ctx, t, subDriver.Connections)
-	// we need to sleep because the raw connection notification
-	// is sent before the pq.Listener can reestablish it's listeners
-	time.Sleep(1 * time.Second)
 
-	// ensure our old subscription still fires
-	err = pubber.Publish("test", []byte("hello-again"))
-	require.NoError(t, err)
-
-	// wait for the message on the old subscription
-	_ = testutil.TryReceive(ctx, t, gotChan)
+	// The raw connection notification is sent before the
+	// pq.Listener re-issues LISTEN on the new connection.
+	// Rather than sleeping a fixed duration, retry publishing
+	// until the subscriber receives a message, which proves
+	// that the LISTEN has been re-established.
+	testutil.Eventually(ctx, t, func(_ context.Context) bool {
+		// Drain any stale signals before publishing.
+		select {
+		case <-gotChan:
+		default:
+		}
+		err := pubber.Publish("test", []byte("hello-again"))
+		if err != nil {
+			return false
+		}
+		select {
+		case <-gotChan:
+			return true
+		case <-time.After(testutil.IntervalFast):
+			return false
+		}
+	}, testutil.IntervalMedium, "subscriber did not receive message after reconnect")
 }
diff --git a/coderd/provisionerjobs_test.go b/coderd/provisionerjobs_test.go
index 91096e3b64..6584b6e241 100644
--- a/coderd/provisionerjobs_test.go
+++ b/coderd/provisionerjobs_test.go
@@ -6,7 +6,6 @@ import (
 	"encoding/json"
 	"strconv"
 	"testing"
-	"time"
 
 	"github.com/google/uuid"
 	"github.com/stretchr/testify/assert"
@@ -28,7 +27,7 @@ func TestProvisionerJobs(t *testing.T) {
 	t.Parallel()
 
 	t.Run("ProvisionerJobs", func(t *testing.T) {
-		db, ps := dbtestutil.NewDB(t, dbtestutil.WithDumpOnFailure())
+		db, ps, sqlDB := dbtestutil.NewDBWithSQLDB(t, dbtestutil.WithDumpOnFailure())
 		client := coderdtest.New(t, &coderdtest.Options{
 			IncludeProvisionerDaemon: true,
 			Database:                 db,
@@ -42,10 +41,17 @@ func TestProvisionerJobs(t *testing.T) {
 		coderdtest.AwaitTemplateVersionJobCompleted(t, client, version.ID)
 		template := coderdtest.CreateTemplate(t, client, owner.OrganizationID, version.ID)
 
-		time.Sleep(1500 * time.Millisecond) // Ensure the workspace build job has a different timestamp for sorting.
 		workspace := coderdtest.CreateWorkspace(t, client, template.ID)
 		coderdtest.AwaitWorkspaceBuildJobCompleted(t, client, workspace.LatestBuild.ID)
 
+		// Ensure the workspace build job has a different timestamp from
+		// the template version job for sorting, without sleeping.
+		_, err := sqlDB.ExecContext(context.Background(),
+			"UPDATE provisioner_jobs SET created_at = created_at + INTERVAL '2 seconds' WHERE id = $1",
+			workspace.LatestBuild.Job.ID,
+		)
+		require.NoError(t, err)
+
 		// Create a pending job.
 		w := dbgen.Workspace(t, db, database.WorkspaceTable{
 			OrganizationID: owner.OrganizationID,