diff --git a/cli/agent.go b/cli/agent.go
index 47552fb..a6ba5a1 100644
--- a/cli/agent.go
+++ b/cli/agent.go
@@ -15,7 +15,7 @@ import (
 )
 
 const (
-	agentVersionIOS     = "0.0.22"
+	agentVersionIOS     = "0.0.23"
 	agentVersionAndroid = "1.2.4"
 	iosRunnerBundleID   = "com.mobilenext.devicekit-iosUITests.xctrunner"
 	androidPackageName  = "com.mobilenext.devicekit"
@@ -23,9 +23,9 @@ const (
 
 // pinned SHA-256 checksums for agent artifacts, keyed by download filename
 var agentChecksums = map[string]string{
-	"devicekit-ios-Sim-arm64.zip":  "0ee133ef245a2b1a5097123be2a43acac8975ab23e708e3b31f94b5074b84dfc",
-	"devicekit-ios-Sim-x86_64.zip": "4d0ab31b0ce1bb977a7196c15ef097a3268bff9f442f37b09da9b330fe76ddac",
-	"devicekit-ios-runner.ipa":     "3704509ea7ce17a47e3ffa6c16fb11ebf706321e008a947cfdab4bc0cfed3416",
+	"devicekit-ios-Sim-arm64.zip":  "db7cc329f8d756be9ad60cf15ae57107ed831c53d35be240708dd2baf8da2d4e",
+	"devicekit-ios-Sim-x86_64.zip": "9de3e48798a6abf600c1bdddefcd3465e2ecccdf373683358b10183e680d6e3a",
+	"devicekit-ios-runner.ipa":     "38e052df988101cba2820c01ba14b6e7193470ca729d4b86a6e44a9a4fbb55fa",
 	"devicekit.apk":                "63b1111fbd3b986c7452bc7c28150b1e9c0d611b2ecd7f6917a0f50a84d0836b",
 }
 
diff --git a/devices/devicekit/requests.go b/devices/devicekit/requests.go
index e980529..5ca46ab 100644
--- a/devices/devicekit/requests.go
+++ b/devices/devicekit/requests.go
@@ -7,11 +7,14 @@ import (
 	"fmt"
 	"io"
 	"net/http"
+	"strings"
 	"time"
 
 	"github.com/mobile-next/mobilecli/utils"
 )
 
+type AgentStartupDiagnostic func() (string, error)
+
 type jsonRPCRequest struct {
 	JSONRPC string `json:"jsonrpc"`
 	Method  string `json:"method"`
@@ -85,6 +88,10 @@ func (c *WdaClient) CallRPCWithTimeout(method string, params any, timeout time.D
 }
 
 func (c *WdaClient) WaitForAgent() error {
+	return c.WaitForAgentWithDiagnostics(nil)
+}
+
+func (c *WdaClient) WaitForAgentWithDiagnostics(readDiagnostic AgentStartupDiagnostic) error {
 	// Set timeout for the entire operation
 	ctx, cancel := context.WithTimeout(context.Background(), 20*time.Second)
 	defer cancel()
@@ -95,12 +102,19 @@ func (c *WdaClient) WaitForAgent() error {
 	for {
 		select {
 		case <-ctx.Done():
+			if diagnostic := readAgentStartupDiagnostic(readDiagnostic); diagnostic != "" {
+				return fmt.Errorf("timed out waiting for WebDriverAgent to be ready; agent stderr:\n%s", diagnostic)
+			}
 			return fmt.Errorf("timed out waiting for WebDriverAgent to be ready")
 
 		case <-ticker.C:
 			_, err := c.GetStatus()
 			if err != nil {
 				utils.Verbose("WebDriverAgent not ready yet: %v", err)
+				diagnostic := readAgentStartupDiagnostic(readDiagnostic)
+				if isFatalAgentStartupDiagnostic(diagnostic) {
+					return fmt.Errorf("WebDriverAgent failed to start:\n%s", diagnostic)
+				}
 				continue
 			}
 
@@ -109,3 +123,23 @@ func (c *WdaClient) WaitForAgent() error {
 		}
 	}
 }
+
+func readAgentStartupDiagnostic(readDiagnostic AgentStartupDiagnostic) string {
+	if readDiagnostic == nil {
+		return ""
+	}
+
+	diagnostic, err := readDiagnostic()
+	if err != nil {
+		utils.Verbose("Failed to read WebDriverAgent startup diagnostics: %v", err)
+		return ""
+	}
+
+	return strings.TrimSpace(diagnostic)
+}
+
+func isFatalAgentStartupDiagnostic(diagnostic string) bool {
+	return strings.Contains(diagnostic, "Library not loaded:") ||
+		strings.Contains(diagnostic, "Termination Reason:") ||
+		strings.Contains(diagnostic, "Fatal error:")
+}
diff --git a/devices/simulator.go b/devices/simulator.go
index e5c1664..1640649 100644
--- a/devices/simulator.go
+++ b/devices/simulator.go
@@ -29,6 +29,7 @@ type AppInfo struct {
 	CFBundleIdentifier  string `json:"CFBundleIdentifier"`
 	CFBundleDisplayName string `json:"CFBundleDisplayName"`
 	CFBundleVersion     string `json:"CFBundleVersion"`
+	Path                string `json:"Path"`
 }
 
 // devicePlist represents the structure of device.plist
@@ -198,8 +199,16 @@ func filterSimulatorsByDownloadsDirectory(simulators []Simulator) []Simulator {
 }
 
 func (s SimulatorDevice) LaunchAppWithEnv(bundleID string, env map[string]string) error {
+	return s.launchAppWithEnv(bundleID, env, "")
+}
+
+func (s SimulatorDevice) launchAppWithEnv(bundleID string, env map[string]string, stderrPath string) error {
 	// Build simctl command
-	fullArgs := append([]string{"simctl", "launch"}, s.UDID, bundleID)
+	fullArgs := []string{"simctl", "launch"}
+	if stderrPath != "" {
+		fullArgs = append(fullArgs, "--stderr="+stderrPath)
+	}
+	fullArgs = append(fullArgs, s.UDID, bundleID)
 	cmd := exec.Command("xcrun", fullArgs...)
 
 	// Set environment variables with SIMCTL_CHILD_ prefix for this command only
@@ -215,6 +224,13 @@ func (s SimulatorDevice) LaunchAppWithEnv(bundleID string, env map[string]string
 	return nil
 }
 
+func simulatorAgentDiagnosticPaths(homeDir string, udid string, launchID int64) (string, string) {
+	filename := fmt.Sprintf("devicekit-agent-%d.stderr", launchID)
+	simulatorPath := filepath.Join("/private/tmp", filename)
+	hostPath := filepath.Join(homeDir, "Library", "Developer", "CoreSimulator", "Devices", udid, "data", "tmp", filename)
+	return simulatorPath, hostPath
+}
+
 func (s SimulatorDevice) LaunchApp(bundleID string, opts LaunchOptions) error {
 	if opts.Activity != "" {
 		return fmt.Errorf("--activity is not supported on iOS")
@@ -469,7 +485,19 @@ func (s *SimulatorDevice) StartAgent(config StartAgentConfig) error {
 		"DEVICEKIT_LISTEN_PORT": strconv.Itoa(usePort),
 	}
 
-	err = s.LaunchAppWithEnv(agentBundleID, env)
+	homeDir, err := os.UserHomeDir()
+	if err != nil {
+		return fmt.Errorf("failed to locate simulator startup diagnostics: %w", err)
+	}
+
+	simulatorStderrPath, hostStderrPath := simulatorAgentDiagnosticPaths(homeDir, s.UDID, time.Now().UnixNano())
+	defer func() {
+		if err := os.Remove(hostStderrPath); err != nil && !os.IsNotExist(err) {
+			utils.Verbose("Failed to remove WebDriverAgent startup diagnostics: %v", err)
+		}
+	}()
+
+	err = s.launchAppWithEnv(agentBundleID, env, simulatorStderrPath)
 	if err != nil {
 		return err
 	}
@@ -481,7 +509,16 @@ func (s *SimulatorDevice) StartAgent(config StartAgentConfig) error {
 		config.OnProgress("Waiting for agent to start")
 	}
 
-	err = s.wdaClient.WaitForAgent()
+	err = s.wdaClient.WaitForAgentWithDiagnostics(func() (string, error) {
+		contents, err := os.ReadFile(hostStderrPath)
+		if os.IsNotExist(err) {
+			return "", nil
+		}
+		if err != nil {
+			return "", err
+		}
+		return string(contents), nil
+	})
 	if err != nil {
 		_ = s.TerminateApp(agentBundleID)
 		return err
@@ -537,10 +574,20 @@ func (s *SimulatorDevice) ListApps(onlyLaunchable bool) ([]InstalledAppInfo, err
 
 	var apps []InstalledAppInfo
 	for _, app := range appsMap {
+		version := app.CFBundleVersion
+		if app.Path != "" {
+			metadata, metadataErr := utils.ParseAppMetadata(app.Path)
+			if metadataErr != nil {
+				utils.Verbose("failed to read app metadata at %s, using build version %s: %v", app.Path, app.CFBundleVersion, metadataErr)
+			} else if metadata.Version != "" {
+				version = metadata.Version
+			}
+		}
+
 		apps = append(apps, InstalledAppInfo{
 			PackageName: app.CFBundleIdentifier,
 			AppName:     app.CFBundleDisplayName,
-			Version:     app.CFBundleVersion,
+			Version:     version,
 		})
 	}