diff --git a/coderd/coderdtest/coderdtest.go b/coderd/coderdtest/coderdtest.go
index b9097863a5f67..0f0a99807a37d 100644
--- a/coderd/coderdtest/coderdtest.go
+++ b/coderd/coderdtest/coderdtest.go
@@ -405,6 +405,12 @@ func NewOptions(t testing.TB, options *Options) (func(http.Handler), context.Can
 		workspacestats.TrackerWithTickFlush(options.WorkspaceUsageTrackerTick, options.WorkspaceUsageTrackerFlush),
 	)
 
+	// create the TempDir for the HTTP file cache BEFORE we start the server and set a t.Cleanup to close it. TempDir()
+	// registers a Cleanup function that deletes the directory, and Cleanup functions are called in reverse order. If
+	// we don't do this, then we could try to delete the directory before the HTTP server is done with all files in it,
+	// which on Windows will fail (can't delete files until all programs have closed handles to them).
+	cacheDir := t.TempDir()
+
 	var mutex sync.RWMutex
 	var handler http.Handler
 	srv := httptest.NewUnstartedServer(http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {
@@ -515,7 +521,7 @@ func NewOptions(t testing.TB, options *Options) (func(http.Handler), context.Can
 			AppHostname:                    options.AppHostname,
 			AppHostnameRegex:               appHostnameRegex,
 			Logger:                         *options.Logger,
-			CacheDir:                       t.TempDir(),
+			CacheDir:                       cacheDir,
 			RuntimeConfig:                  runtimeManager,
 			Database:                       options.Database,
 			Pubsub:                         options.Pubsub,