diff --git a/backends/postgres/postgres_backend.go b/backends/postgres/postgres_backend.go
index 247c4ba..8826329 100644
--- a/backends/postgres/postgres_backend.go
+++ b/backends/postgres/postgres_backend.go
@@ -848,6 +848,9 @@ func (p *PgBackend) handleJob(ctx context.Context, jobID string) (err error) {
 		return
 	}
 
+	ctx = withJobContext(ctx, job)
+	ctx = context.WithValue(ctx, txCtxVarKey, tx)
+
 	if job.Deadline != nil && job.Deadline.Before(time.Now().UTC()) {
 		err = jobs.ErrJobExceededDeadline
 		p.logger.Debug("job deadline is in the past, skipping", slog.String("queue", job.Queue), slog.Int64("job_id", job.ID))
@@ -855,9 +858,6 @@ func (p *PgBackend) handleJob(ctx context.Context, jobID string) (err error) {
 		return
 	}
 
-	ctx = withJobContext(ctx, job)
-	ctx = context.WithValue(ctx, txCtxVarKey, tx)
-
 	// check if the job is being retried and increment retry count accordingly
 	if job.Status != internal.JobStatusNew {
 		job.Retries++
diff --git a/backends/postgres/postgres_backend_test.go b/backends/postgres/postgres_backend_test.go
index 9e2bcb5..63d4540 100644
--- a/backends/postgres/postgres_backend_test.go
+++ b/backends/postgres/postgres_backend_test.go
@@ -999,3 +999,49 @@ func TestGetPQConnectionString(t *testing.T) {
 		})
 	}
 }
+
+// TestJobWithPastDeadline ensures that when a job is scheduled and its deadline is in the past, that the job is updated
+// with an error indicating that its deadline was not met
+// https://github.com/acaloiaro/neoq/issues/123
+func TestJobWithPastDeadline(t *testing.T) {
+	connString, _ := prepareAndCleanupDB(t)
+	const queue = "testing"
+	maxRetries := 5
+	done := make(chan bool)
+	defer close(done)
+
+	ctx := context.Background()
+	nq, err := neoq.New(ctx, neoq.WithBackend(postgres.Backend), postgres.WithConnectionString(connString))
+	if err != nil {
+		t.Fatal(err)
+	}
+	defer nq.Shutdown(ctx)
+
+	h := handler.New(queue, func(_ context.Context) (err error) {
+		done <- true
+		return
+	})
+
+	err = nq.Start(ctx, h)
+	if err != nil {
+		t.Error(err)
+	}
+
+	// deadline in the past
+	deadline := time.Now().UTC().Add(time.Duration(-5) * time.Second)
+	jid, e := nq.Enqueue(ctx, &jobs.Job{
+		Queue: queue,
+		Payload: map[string]interface{}{
+			"message": "hello world",
+		},
+		Deadline:   &deadline,
+		MaxRetries: &maxRetries,
+	})
+	if e != nil || jid == jobs.DuplicateJobID {
+		t.Error(e)
+	}
+
+	if e != nil && !errors.Is(e, jobs.ErrJobExceededDeadline) {
+		t.Error(err)
+	}
+}
diff --git a/flake.nix b/flake.nix
index cd68305..b79134a 100644
--- a/flake.nix
+++ b/flake.nix
@@ -22,7 +22,7 @@
   in {
     devShells = forEachSystem (system: let
       pkgs = nixpkgs.legacyPackages.${system};
-      postgresPort = 5433;
+      postgresPort = 5434;
       redisPort = 6380;
     in {
       default = devenv.lib.mkShell {