diff --git a/coderd/x/chatd/chatd.go b/coderd/x/chatd/chatd.go
index 45a0fdd46b..f6b52e8201 100644
--- a/coderd/x/chatd/chatd.go
+++ b/coderd/x/chatd/chatd.go
@@ -869,6 +869,10 @@ func (p *Server) CreateChat(ctx context.Context, opts CreateOptions) (database.C
 	if opts.Labels == nil {
 		opts.Labels = database.StringMap{}
 	}
+	// Resolve the deployment prompt before opening the transaction so
+	// chat creation does not hold one DB connection while waiting for
+	// another pool checkout.
+	deploymentPrompt := p.resolveDeploymentSystemPrompt(ctx)
 
 	var chat database.Chat
 	txErr := p.db.InTx(func(tx database.Store) error {
@@ -904,7 +908,6 @@ func (p *Server) CreateChat(ctx context.Context, opts CreateOptions) (database.C
 			return xerrors.Errorf("insert chat: %w", err)
 		}
 
-		deploymentPrompt := p.resolveDeploymentSystemPrompt(ctx)
 		userPrompt := SanitizePromptText(opts.SystemPrompt)
 		var workspaceAwareness string
 		if opts.WorkspaceID.Valid {