diff --git a/coderd/httpapi/httpapi.go b/coderd/httpapi/httpapi.go
index a42b79eaa4..5e4648828f 100644
--- a/coderd/httpapi/httpapi.go
+++ b/coderd/httpapi/httpapi.go
@@ -6,14 +6,13 @@ import (
 	"encoding/json"
 	"errors"
 	"fmt"
-	"io"
 	"net/http"
 	"reflect"
 	"strings"
-	"sync"
 	"time"
 
 	"github.com/go-playground/validator/v10"
+	"golang.org/x/xerrors"
 
 	"github.com/coder/coder/coderd/tracing"
 	"github.com/coder/coder/codersdk"
@@ -174,8 +173,7 @@ func WebsocketCloseSprintf(format string, vars ...any) string {
 	return msg
 }
 
-func ServerSentEventSender(rw http.ResponseWriter, r *http.Request) (func(ctx context.Context, sse codersdk.ServerSentEvent) error, error) {
-	var mu sync.Mutex
+func ServerSentEventSender(rw http.ResponseWriter, r *http.Request) (sendEvent func(ctx context.Context, sse codersdk.ServerSentEvent) error, closed chan struct{}, err error) {
 	h := rw.Header()
 	h.Set("Content-Type", "text/event-stream")
 	h.Set("Cache-Control", "no-cache")
@@ -187,37 +185,50 @@ func ServerSentEventSender(rw http.ResponseWriter, r *http.Request) (func(ctx co
 		panic("http.ResponseWriter is not http.Flusher")
 	}
 
-	// Send a heartbeat every 15 seconds to avoid the connection being killed.
+	closed = make(chan struct{})
+	type sseEvent struct {
+		payload []byte
+		errC    chan error
+	}
+	eventC := make(chan sseEvent)
+
+	// Synchronized handling of events (no guarantee of order).
 	go func() {
+		defer close(closed)
+
+		// Send a heartbeat every 15 seconds to avoid the connection being killed.
 		ticker := time.NewTicker(time.Second * 15)
 		defer ticker.Stop()
 
 		for {
+			var event sseEvent
+
 			select {
 			case <-r.Context().Done():
 				return
+			case event = <-eventC:
 			case <-ticker.C:
-				mu.Lock()
-				_, err := io.WriteString(rw, fmt.Sprintf("event: %s\n\n", codersdk.ServerSentEventTypePing))
-				if err != nil {
-					mu.Unlock()
-					return
+				event = sseEvent{
+					payload: []byte(fmt.Sprintf("event: %s\n\n", codersdk.ServerSentEventTypePing)),
 				}
-				f.Flush()
-				mu.Unlock()
 			}
+
+			_, err := rw.Write(event.payload)
+			if event.errC != nil {
+				event.errC <- err
+			}
+			if err != nil {
+				return
+			}
+			f.Flush()
 		}
 	}()
 
-	sendEvent := func(ctx context.Context, sse codersdk.ServerSentEvent) error {
-		if ctx.Err() != nil {
-			return ctx.Err()
-		}
-
+	sendEvent = func(ctx context.Context, sse codersdk.ServerSentEvent) error {
 		buf := &bytes.Buffer{}
 		enc := json.NewEncoder(buf)
 
-		_, err := buf.Write([]byte(fmt.Sprintf("event: %s\ndata: ", sse.Type)))
+		_, err := buf.WriteString(fmt.Sprintf("event: %s\ndata: ", sse.Type))
 		if err != nil {
 			return err
 		}
@@ -232,16 +243,32 @@ func ServerSentEventSender(rw http.ResponseWriter, r *http.Request) (func(ctx co
 			return err
 		}
 
-		mu.Lock()
-		defer mu.Unlock()
-		_, err = rw.Write(buf.Bytes())
-		if err != nil {
-			return err
+		event := sseEvent{
+			payload: buf.Bytes(),
+			errC:    make(chan error, 1), // Buffered to prevent deadlock.
 		}
-		f.Flush()
 
-		return nil
+		select {
+		case <-r.Context().Done():
+			return r.Context().Err()
+		case <-ctx.Done():
+			return ctx.Err()
+		case <-closed:
+			return xerrors.New("server sent event sender closed")
+		case eventC <- event:
+			// Re-check closure signals after sending the event to allow
+			// for early exit. We don't check closed here because it
+			// can't happen while processing the event.
+			select {
+			case <-r.Context().Done():
+				return r.Context().Err()
+			case <-ctx.Done():
+				return ctx.Err()
+			case err := <-event.errC:
+				return err
+			}
+		}
 	}
 
-	return sendEvent, nil
+	return sendEvent, closed, nil
 }
diff --git a/coderd/workspaces.go b/coderd/workspaces.go
index 0295dc29d5..2b3d077d10 100644
--- a/coderd/workspaces.go
+++ b/coderd/workspaces.go
@@ -867,7 +867,7 @@ func (api *API) watchWorkspace(rw http.ResponseWriter, r *http.Request) {
 		return
 	}
 
-	sendEvent, err := httpapi.ServerSentEventSender(rw, r)
+	sendEvent, senderClosed, err := httpapi.ServerSentEventSender(rw, r)
 	if err != nil {
 		httpapi.Write(ctx, rw, http.StatusInternalServerError, codersdk.Response{
 			Message: "Internal error setting up server-sent events.",
@@ -875,6 +875,10 @@ func (api *API) watchWorkspace(rw http.ResponseWriter, r *http.Request) {
 		})
 		return
 	}
+	// Prevent handler from returning until the sender is closed.
+	defer func() {
+		<-senderClosed
+	}()
 
 	// Ignore all trace spans after this, they're not too useful.
 	ctx = trace.ContextWithSpan(ctx, tracing.NoopSpan)
@@ -885,6 +889,8 @@ func (api *API) watchWorkspace(rw http.ResponseWriter, r *http.Request) {
 		select {
 		case <-ctx.Done():
 			return
+		case <-senderClosed:
+			return
 		case <-t.C:
 			workspace, err := api.Database.GetWorkspaceByID(ctx, workspace.ID)
 			if err != nil {