diff --git a/coderd/workspaceagents.go b/coderd/workspaceagents.go
index b881e337906ba..f2d3acfb742dd 100644
--- a/coderd/workspaceagents.go
+++ b/coderd/workspaceagents.go
@@ -1434,9 +1434,6 @@ func (api *API) watchWorkspaceAgentMetadata(rw http.ResponseWriter, r *http.Requ
 		})
 	}
 
-	// Send initial metadata.
-	sendMetadata(true)
-
 	// We debounce metadata updates to avoid overloading the frontend when
 	// an agent is sending a lot of updates.
 	pubsubDebounce := debounce.New(time.Second)
@@ -1444,7 +1441,8 @@ func (api *API) watchWorkspaceAgentMetadata(rw http.ResponseWriter, r *http.Requ
 		pubsubDebounce = debounce.New(time.Millisecond * 100)
 	}
 
-	// Send metadata on updates.
+	// Send metadata on updates, we must ensure subscription before sending
+	// initial metadata to guarantee that events in-between are not missed.
 	cancelSub, err := api.Pubsub.Subscribe(watchWorkspaceAgentMetadataChannel(workspaceAgent.ID), func(_ context.Context, _ []byte) {
 		pubsubDebounce(func() {
 			sendMetadata(true)
@@ -1456,12 +1454,14 @@ func (api *API) watchWorkspaceAgentMetadata(rw http.ResponseWriter, r *http.Requ
 	}
 	defer cancelSub()
 
+	// Send initial metadata.
+	sendMetadata(true)
+
 	for {
 		select {
 		case <-senderClosed:
 			return
 		case <-refreshTicker.C:
-			break
 		}
 
 		// Avoid spamming the DB with reads we know there are no updates. We want
diff --git a/coderd/workspaceagents_test.go b/coderd/workspaceagents_test.go
index 73b540ea5ac68..2a514385d94df 100644
--- a/coderd/workspaceagents_test.go
+++ b/coderd/workspaceagents_test.go
@@ -1268,11 +1268,6 @@ func TestWorkspaceAgent_Metadata(t *testing.T) {
 
 	var update []codersdk.WorkspaceAgentMetadata
 
-	check := func(want codersdk.WorkspaceAgentMetadataResult, got codersdk.WorkspaceAgentMetadata) {
-		require.Equal(t, want.Value, got.Result.Value)
-		require.Equal(t, want.Error, got.Result.Error)
-	}
-
 	wantMetadata1 := codersdk.WorkspaceAgentMetadataResult{
 		CollectedAt: time.Now(),
 		Value:       "bar",
@@ -1285,17 +1280,38 @@ func TestWorkspaceAgent_Metadata(t *testing.T) {
 
 	recvUpdate := func() []codersdk.WorkspaceAgentMetadata {
 		select {
+		case <-ctx.Done():
+			t.Fatalf("context done: %v", ctx.Err())
 		case err := <-errors:
 			t.Fatalf("error watching metadata: %v", err)
-			return nil
 		case update := <-updates:
 			return update
 		}
+		return nil
+	}
+
+	check := func(want codersdk.WorkspaceAgentMetadataResult, got codersdk.WorkspaceAgentMetadata, retry bool) {
+		// We can't trust the order of the updates due to timers and debounces,
+		// so let's check a few times more.
+		for i := 0; retry && i < 2 && (want.Value != got.Result.Value || want.Error != got.Result.Error); i++ {
+			update = recvUpdate()
+			for _, m := range update {
+				if m.Description.Key == got.Description.Key {
+					got = m
+					break
+				}
+			}
+		}
+		ok1 := assert.Equal(t, want.Value, got.Result.Value)
+		ok2 := assert.Equal(t, want.Error, got.Result.Error)
+		if !ok1 || !ok2 {
+			require.FailNow(t, "check failed")
+		}
 	}
 
 	update = recvUpdate()
 	require.Len(t, update, 3)
-	check(wantMetadata1, update[0])
+	check(wantMetadata1, update[0], false)
 	// The second metadata result is not yet posted.
 	require.Zero(t, update[1].Result.CollectedAt)
 
@@ -1303,14 +1319,14 @@ func TestWorkspaceAgent_Metadata(t *testing.T) {
 	post("foo2", wantMetadata2)
 	update = recvUpdate()
 	require.Len(t, update, 3)
-	check(wantMetadata1, update[0])
-	check(wantMetadata2, update[1])
+	check(wantMetadata1, update[0], true)
+	check(wantMetadata2, update[1], true)
 
 	wantMetadata1.Error = "error"
 	post("foo1", wantMetadata1)
 	update = recvUpdate()
 	require.Len(t, update, 3)
-	check(wantMetadata1, update[0])
+	check(wantMetadata1, update[0], true)
 
 	const maxValueLen = 32 << 10
 	tooLongValueMetadata := wantMetadata1
@@ -1319,6 +1335,9 @@ func TestWorkspaceAgent_Metadata(t *testing.T) {
 	tooLongValueMetadata.CollectedAt = time.Now()
 	post("foo3", tooLongValueMetadata)
 	got := recvUpdate()[2]
+	for i := 0; i < 2 && len(got.Result.Value) != maxValueLen; i++ {
+		got = recvUpdate()[2]
+	}
 	require.Len(t, got.Result.Value, maxValueLen)
 	require.NotEmpty(t, got.Result.Error)
 
diff --git a/codersdk/workspaceagents.go b/codersdk/workspaceagents.go
index b99185bd7cc8d..34397e89c43f7 100644
--- a/codersdk/workspaceagents.go
+++ b/codersdk/workspaceagents.go
@@ -304,6 +304,7 @@ func (c *Client) WatchWorkspaceAgentMetadata(ctx context.Context, id uuid.UUID)
 
 	metadataChan := make(chan []WorkspaceAgentMetadata, 256)
 
+	ready := make(chan struct{})
 	watch := func() error {
 		res, err := c.Request(ctx, http.MethodGet, fmt.Sprintf("/api/v2/workspaceagents/%s/watch-metadata", id), nil)
 		if err != nil {
@@ -316,12 +317,12 @@ func (c *Client) WatchWorkspaceAgentMetadata(ctx context.Context, id uuid.UUID)
 		nextEvent := ServerSentEventReader(ctx, res.Body)
 		defer res.Body.Close()
 
+		firstEvent := true
 		for {
 			select {
 			case <-ctx.Done():
 				return ctx.Err()
 			default:
-				break
 			}
 
 			sse, err := nextEvent()
@@ -329,6 +330,11 @@ func (c *Client) WatchWorkspaceAgentMetadata(ctx context.Context, id uuid.UUID)
 				return err
 			}
 
+			if firstEvent {
+				close(ready) // Only close ready after the first event is received.
+				firstEvent = false
+			}
+
 			b, ok := sse.Data.([]byte)
 			if !ok {
 				return xerrors.Errorf("unexpected data type: %T", sse.Data)
@@ -358,9 +364,18 @@ func (c *Client) WatchWorkspaceAgentMetadata(ctx context.Context, id uuid.UUID)
 	errorChan := make(chan error, 1)
 	go func() {
 		defer close(errorChan)
-		errorChan <- watch()
+		err := watch()
+		select {
+		case <-ready:
+		default:
+			close(ready) // Error before first event.
+		}
+		errorChan <- err
 	}()
 
+	// Wait until first event is received and the subscription is registered.
+	<-ready
+
 	return metadataChan, errorChan
 }