diff --git a/cmd/dev.go b/cmd/dev.go
index ed6ef7a6..82e47f95 100644
--- a/cmd/dev.go
+++ b/cmd/dev.go
@@ -2,6 +2,7 @@ package cmd
 
 import (
 	"context"
+	"errors"
 	"fmt"
 	"io"
 	"os"
@@ -123,6 +124,10 @@ Examples:
 		tuiLoggerErr := dev.NewTUILogger(logLevel, ui, dev.StdErr)
 
 		if err := server.Connect(ui, tuiLogger, tuiLoggerErr); err != nil {
+			if errors.Is(err, context.Canceled) {
+				ui.Close(true)
+				return
+			}
 			log.Error("failed to start live dev connection: %s", err)
 			ui.Close(true)
 			return
diff --git a/internal/bundler/shim.go b/internal/bundler/shim.go
index 6eb4c0a0..206a0472 100644
--- a/internal/bundler/shim.go
+++ b/internal/bundler/shim.go
@@ -69,39 +69,43 @@ function getSourceMap(filename) {
 }
 const frameRegex = /(.+)\((.+):(\d+):(\d+)\)$/;
 Error.prepareStackTrace = function (err, stack) {
-	const _stack = __prepareStackTrace(err, stack);
-	const tok = _stack.split('\n');
-	const lines = [];
-	for (const t of tok) {
-		if (t.includes('.agentuity/') && frameRegex.test(t)) {
-			const parts = frameRegex.exec(t);
-			if (parts.length === 5) {
-				const filename = parts[2];
-				const sm = getSourceMap(filename+'.map');
-				if (sm) {
-					const lineno = parts[3];
-					const colno = parts[4];
-					const pos = sm.originalPositionFor({
-						line: +lineno,
-						column: +colno,
-					})
-					if (pos && pos.source) {
-						const startIndex = filename.indexOf('.agentuity/');
-						const offset = filename.includes('../node_modules/') ? 11 : 0;
-						const basedir = filename.substring(0, startIndex + offset);
-						const sourceOffset = pos.source.indexOf('src/');
-						const source = pos.source.substring(sourceOffset);
-						const newfile = __agentuity_join(basedir, source);
-						const newline = parts[1] + '(' + newfile + ':' + pos.line + ':' + pos.column + ')';
-						lines.push(newline);
-						continue;
+	try {
+		const _stack = __prepareStackTrace(err, stack);
+		const tok = _stack.split('\n');
+		const lines = [];
+		for (const t of tok) {
+			if (t.includes('.agentuity/') && frameRegex.test(t)) {
+				const parts = frameRegex.exec(t);
+				if (parts.length === 5) {
+					const filename = parts[2];
+					const sm = getSourceMap(filename+'.map');
+					if (sm) {
+						const lineno = parts[3];
+						const colno = parts[4];
+						const pos = sm.originalPositionFor({
+							line: +lineno,
+							column: +colno,
+						})
+						if (pos && pos.source) {
+							const startIndex = filename.indexOf('.agentuity/');
+							const offset = filename.includes('../node_modules/') ? 11 : 0;
+							const basedir = filename.substring(0, startIndex + offset);
+							const sourceOffset = pos.source.indexOf('src/');
+							const source = pos.source.substring(sourceOffset);
+							const newfile = __agentuity_join(basedir, source);
+							const newline = parts[1] + '(' + newfile + ':' + pos.line + ':' + pos.column + ')';
+							lines.push(newline);
+							continue;
+						}
 					}
 				}
 			}
+			lines.push(t);
 		}
-		lines.push(t);
+		return lines.join('\n');
+	} catch (e) {
+		return stack;
 	}
-	return lines.join('\n');
 };
 })();
 `
diff --git a/internal/dev/server.go b/internal/dev/server.go
index dd147199..7a8a8efc 100644
--- a/internal/dev/server.go
+++ b/internal/dev/server.go
@@ -56,7 +56,7 @@ type Server struct {
 	apiclient      *util.APIClient
 	publicUrl      string
 	port           int
-	connected      chan string
+	connected      chan error
 	pendingLogger  logger.Logger
 	expiresAt      *time.Time
 	tlsCertificate *tls.Certificate
@@ -161,6 +161,8 @@ func (s *Server) reconnect() {
 func (s *Server) connect(initial bool) {
 	var gerr error
 
+	s.logger.Trace("connecting to devmode server")
+
 	// hold a connection lock to prevent multiple go routines from trying to reconnect
 	// before the previous connect goroutine has finished
 	s.connectionLock.Lock()
@@ -168,7 +170,7 @@ func (s *Server) connect(initial bool) {
 
 	defer func() {
 		if initial && gerr != nil {
-			s.connected <- gerr.Error()
+			s.connected <- gerr
 		}
 		s.logger.Debug("connection closed")
 		select {
@@ -201,12 +203,19 @@ func (s *Server) connect(initial bool) {
 		}
 	}()
 
+	s.logger.Trace("refreshing connection metadata")
+	refreshStart := time.Now()
 	if err := s.refreshConnection(); err != nil {
-		s.logger.Error("failed to refresh connection: %s", err)
+		if !initial {
+			s.logger.Error("failed to refresh connection: %s", err)
+		}
+		// initial will bubble this up
 		gerr = err
 		return
 	}
 
+	s.logger.Trace("refreshed connection metadata in %v", time.Since(refreshStart))
+
 	var tlsConfig tls.Config
 	tlsConfig.Certificates = []tls.Certificate{*s.tlsCertificate}
 	tlsConfig.NextProtos = []string{"h2"}
@@ -221,6 +230,8 @@ func (s *Server) connect(initial bool) {
 		hostname = fmt.Sprintf("%s:443", hostname)
 	}
 
+	s.logger.Trace("dialing devmode server: %s", hostname)
+	dialStart := time.Now()
 	conn, err := tls.Dial("tcp", hostname, &tlsConfig)
 	if err != nil {
 		gerr = err
@@ -228,9 +239,10 @@ func (s *Server) connect(initial bool) {
 		return
 	}
 	s.conn = conn
+	s.logger.Trace("dialed devmode server in %v", time.Since(dialStart))
 
 	if initial {
-		s.connected <- ""
+		s.connected <- nil
 	}
 
 	// if we successfully connect, reset our connection failures
@@ -557,18 +569,15 @@ func (s *Server) HealthCheck(devModeUrl string) error {
 }
 
 func (s *Server) Connect(ui *DevModeUI, tuiLogger logger.Logger, tuiLoggerErr logger.Logger) error {
-	s.logger = tuiLogger
-	if pl, ok := tuiLoggerErr.(*PendingLogger); ok {
-		pl.drain(ui, tuiLoggerErr)
-	}
 	if pl, ok := s.logger.(*PendingLogger); ok {
-		pl.drain(ui, s.logger)
+		pl.drain(ui, tuiLogger)
 	}
+	s.logger = tuiLogger
 	s.pendingLogger = s.logger
-	msg := <-s.connected
+	err := <-s.connected
 	close(s.connected)
-	if msg != "" {
-		return fmt.Errorf("%s", msg)
+	if err != nil {
+		return err
 	}
 	return nil
 }
@@ -590,11 +599,12 @@ func (s *Server) monitor() {
 }
 
 func New(args ServerArgs) (*Server, error) {
-	id := cstr.NewHash(args.OrgId, args.UserId)
+	id := cstr.NewHash(args.Project.Project.ProjectId, args.UserId)
 	tracer := otel.Tracer("@agentuity/cli", trace.WithInstrumentationAttributes(
 		attribute.String("id", id),
 		attribute.String("@agentuity/orgId", args.OrgId),
 		attribute.String("@agentuity/userId", args.UserId),
+		attribute.String("@agentuity/projectId", args.Project.Project.ProjectId),
 		attribute.Bool("@agentuity/devmode", true),
 		attribute.String("name", "@agentuity/cli"),
 		attribute.String("version", args.Version),
@@ -618,9 +628,9 @@ func New(args ServerArgs) (*Server, error) {
 		tracer:        tracer,
 		version:       args.Version,
 		port:          args.Port,
-		apiclient:     util.NewAPIClient(context.Background(), pendingLogger, args.APIURL, args.APIKey),
+		apiclient:     util.NewAPIClient(ctx, pendingLogger, args.APIURL, args.APIKey),
 		pendingLogger: pendingLogger,
-		connected:     make(chan string, 1),
+		connected:     make(chan error, 1),
 	}
 
 	go server.connect(true)
diff --git a/internal/util/api.go b/internal/util/api.go
index 45bfcb0c..8b8279f9 100644
--- a/internal/util/api.go
+++ b/internal/util/api.go
@@ -175,6 +175,9 @@ func (c *APIClient) Do(method, pathParam string, payload interface{}, response i
 			continue
 		}
 		if err != nil {
+			if errors.Is(err, context.Canceled) || errors.Is(err, context.DeadlineExceeded) {
+				return err
+			}
 			return NewAPIError(u.String(), method, 0, "", fmt.Errorf("error sending request: %w", err), traceID)
 		}
 		break