diff --git a/cmd/dev.go b/cmd/dev.go
index 710bc0c9..b4a90991 100644
--- a/cmd/dev.go
+++ b/cmd/dev.go
@@ -73,6 +73,14 @@ Examples:
 			websocketId = cstr.NewHash(orgId, userId)
 		}
 
+		port, _ := cmd.Flags().GetInt("port")
+		if port == 0 {
+			port, err = dev.FindAvailablePort(theproject)
+			if err != nil {
+				log.Fatal("failed to find available port: %s", err)
+			}
+		}
+
 		websocketConn, err := dev.NewWebsocket(dev.WebsocketArgs{
 			Ctx:          ctx,
 			Logger:       log,
@@ -88,11 +96,6 @@ Examples:
 		}
 		defer websocketConn.Close()
 
-		port, err := dev.FindAvailablePort(theproject)
-		if err != nil {
-			log.Fatal("failed to find available port: %s", err)
-		}
-
 		projectServerCmd, err := dev.CreateRunProjectCmd(ctx, log, theproject, websocketConn, dir, orgId, port)
 		if err != nil {
 			errsystem.New(errsystem.ErrInvalidConfiguration, err, errsystem.WithContextMessage("Failed to run project")).ShowErrorAndExit()
@@ -222,6 +225,7 @@ func init() {
 	devCmd.Flags().StringP("dir", "d", ".", "The directory to run the development server in")
 	devCmd.Flags().String("websocket-id", "", "The websocket room id to use for the development agent")
 	devCmd.Flags().String("org-id", "", "The organization to run the project")
+	devCmd.Flags().Int("port", 0, "The port to run the development server on (uses project default if not provided)")
 	devCmd.Flags().MarkHidden("websocket-id")
 	devCmd.Flags().MarkHidden("org-id")
 }
diff --git a/internal/bundler/bundler.go b/internal/bundler/bundler.go
index 6a91748c..d241d8dd 100644
--- a/internal/bundler/bundler.go
+++ b/internal/bundler/bundler.go
@@ -120,7 +120,7 @@ func bundleJavascript(ctx BundleContext, dir string, outdir string, theproject *
 			defines["process.env.AGENTUITY_ENVIRONMENT"] = fmt.Sprintf("'%s'", "development")
 		}
 	}
-	defines["process.env.AGENTUITY_CLOUD_AGENTS_JSON"] = fmt.Sprintf("'%s'", cstr.JSONStringify(agents))
+	defines["process.env.AGENTUITY_CLOUD_AGENTS_JSON"] = cstr.JSONStringify(cstr.JSONStringify(agents))
 
 	ctx.Logger.Debug("starting build")
 	started := time.Now()
diff --git a/internal/dev/websocket.go b/internal/dev/websocket.go
index 7526d104..cbd6ec31 100644
--- a/internal/dev/websocket.go
+++ b/internal/dev/websocket.go
@@ -80,27 +80,47 @@ func (c *Websocket) Done() <-chan struct{} {
 	return c.done
 }
 
+const maxHealthCheckDuration = time.Second * 30
+
+func isConnectionErrorRetryable(err error) bool {
+	if strings.Contains(err.Error(), "connection refused") {
+		return true
+	}
+	if strings.Contains(err.Error(), "connection reset by peer") {
+		return true
+	}
+	if strings.Contains(err.Error(), "No connection could be made because the target machine actively refused it") { // windows
+		return true
+	}
+	return false
+}
+
 func (c *Websocket) getAgentProtocol(ctx context.Context, port int) (bool, error) {
 	url := fmt.Sprintf("http://127.0.0.1:%d/_health", port)
-	for i := 0; i < 5; i++ {
+	started := time.Now()
+	var i int
+	for time.Since(started) < maxHealthCheckDuration {
+		i++
 		req, err := http.NewRequestWithContext(ctx, "GET", url, nil)
 		if err != nil {
 			return false, err
 		}
 		resp, err := http.DefaultClient.Do(req)
 		if err != nil {
-			if strings.Contains(err.Error(), "connection refused") {
+			c.logger.Debug("healthcheck attempt #%d failed: %s", i, err)
+			if isConnectionErrorRetryable(err) {
 				time.Sleep(time.Millisecond * time.Duration(100*i+1))
 				continue
 			}
 			return false, err
 		}
+		c.logger.Debug("healthcheck attempt #%d succeeded with status code %d", i, resp.StatusCode)
 		defer resp.Body.Close()
 		if resp.StatusCode == 200 {
 			return resp.Header.Get("x-agentuity-binary") == "true", nil
 		}
 	}
-	return false, fmt.Errorf("failed to inspect agents after 5 attempts")
+	return false, fmt.Errorf("failed to inspect agents after %s", maxHealthCheckDuration)
 }
 
 func (c *Websocket) getAgentWelcome(ctx context.Context, port int) (map[string]Welcome, error) {
@@ -112,7 +132,7 @@ func (c *Websocket) getAgentWelcome(ctx context.Context, port int) (map[string]W
 		}
 		resp, err := http.DefaultClient.Do(req)
 		if err != nil {
-			if strings.Contains(err.Error(), "connection refused") {
+			if isConnectionErrorRetryable(err) {
 				time.Sleep(time.Millisecond * time.Duration(100*i+1))
 				continue
 			}
@@ -135,7 +155,7 @@ func (c *Websocket) StartReadingMessages(ctx context.Context, logger logger.Logg
 	var err error
 	c.binaryProtocol, err = c.getAgentProtocol(ctx, port)
 	if err != nil {
-		logger.Error("failed to healthcheck agents: %s", err)
+		logger.Fatal("Your project failed to start. This typically happens when the project cannot compile or this is an underlying issue with starting the project.")
 		return
 	}
 
diff --git a/internal/project/project.go b/internal/project/project.go
index d9b8ec9c..6493663c 100644
--- a/internal/project/project.go
+++ b/internal/project/project.go
@@ -8,6 +8,7 @@ import (
 	"net/url"
 	"os"
 	"path/filepath"
+	"strings"
 
 	"github.com/Masterminds/semver"
 	"github.com/agentuity/cli/internal/errsystem"
@@ -486,6 +487,13 @@ func LoadProject(logger logger.Logger, dir string, apiUrl string, appUrl string,
 	}
 }
 
+func isVersionCheckRequired(ver string) bool {
+	if ver != "" && ver != "dev" && !strings.Contains(ver, "-next") {
+		return true
+	}
+	return false
+}
+
 func EnsureProject(ctx context.Context, cmd *cobra.Command) ProjectContext {
 	logger := env.NewLogger(cmd)
 	dir := ResolveProjectDir(logger, cmd, true)
@@ -498,7 +506,7 @@ func EnsureProject(ctx context.Context, cmd *cobra.Command) ProjectContext {
 		token, _ = util.EnsureLoggedIn(ctx, logger, cmd)
 	}
 	p := LoadProject(logger, dir, apiUrl, appUrl, transportUrl, token)
-	if !p.NewProject && Version != "" && Version != "dev" && p.Project.Version != "" {
+	if !p.NewProject && isVersionCheckRequired(Version) && p.Project.Version != "" {
 		v := semver.MustParse(Version)
 		c, err := semver.NewConstraint(p.Project.Version)
 		if err != nil {
@@ -538,7 +546,7 @@ func TryProject(ctx context.Context, cmd *cobra.Command) ProjectContext {
 		}
 	}
 	p := LoadProject(logger, dir, apiUrl, appUrl, transportUrl, token)
-	if !p.NewProject && Version != "" && Version != "dev" && p.Project.Version != "" {
+	if !p.NewProject && isVersionCheckRequired(Version) && p.Project.Version != "" {
 		v := semver.MustParse(Version)
 		c, err := semver.NewConstraint(p.Project.Version)
 		if err != nil {