diff --git a/internal/app/app.go b/internal/app/app.go
index 7a7a3b1..5a1092f 100644
--- a/internal/app/app.go
+++ b/internal/app/app.go
@@ -340,7 +340,7 @@ const (
 	DOCKERFILE    = "Dockerfile"
 )
 
-func (a *App) loadContainerManager(dryRun DryRun) error {
+func (a *App) loadContainerManager(stripAppPath bool) error {
 	containerConfig, err := a.appDef.Attr("container")
 	if err != nil || containerConfig == starlark.None {
 		// Plugin not authorized, skip any container files
@@ -447,7 +447,7 @@ func (a *App) loadContainerManager(dryRun DryRun) error {
 	}
 
 	a.containerManager, err = NewContainerManager(a.Logger, a,
-		fileName, a.systemConfig, port, lifetime, scheme, health, buildDir, a.sourceFS, a.paramMap, a.appConfig.Container)
+		fileName, a.systemConfig, port, lifetime, scheme, health, buildDir, a.sourceFS, a.paramMap, a.appConfig.Container, stripAppPath)
 	if err != nil {
 		return fmt.Errorf("error creating container manager: %w", err)
 	}
diff --git a/internal/app/container_manager.go b/internal/app/container_manager.go
index 688c3b9..a9d7f5c 100644
--- a/internal/app/container_manager.go
+++ b/internal/app/container_manager.go
@@ -61,11 +61,12 @@ type ContainerManager struct {
 
 	// Health check related fields
 	healthCheckTicker *time.Ticker
+	stripAppPath      bool
 }
 
 func NewContainerManager(logger *types.Logger, app *App, containerFile string,
 	systemConfig *types.SystemConfig, configPort int64, lifetime, scheme, health, buildDir string, sourceFS appfs.ReadableFS,
-	paramMap map[string]string, containerConfig types.Container) (*ContainerManager, error) {
+	paramMap map[string]string, containerConfig types.Container, stripAppPath bool) (*ContainerManager, error) {
 
 	image := ""
 	volumes := []string{}
@@ -140,6 +141,7 @@ func NewContainerManager(logger *types.Logger, app *App, containerFile string,
 		containerConfig: containerConfig,
 		stateLock:       sync.RWMutex{},
 		currentState:    ContainerStateUnknown,
+		stripAppPath:    stripAppPath,
 	}
 
 	if containerConfig.IdleShutdownSecs > 0 && (!app.IsDev || containerConfig.IdleShutdownDevApps) {
@@ -444,17 +446,29 @@ func (m *ContainerManager) WaitForHealth(attempts int) error {
 
 	var err error
 	var resp *http.Response
+	url := m.GetProxyUrl()
+	if !m.stripAppPath {
+		// Apps like Streamlit require the app path to be present
+		url = url + m.app.Path
+	}
+
+	url += m.health
+
 	for attempt := 1; attempt <= attempts; attempt++ {
-		resp, err = client.Get(m.GetProxyUrl() + m.health)
-		if err == nil && resp.StatusCode == http.StatusOK {
-			return nil
+		resp, err = client.Get(url)
+		statusCode := "N/A"
+		if err == nil {
+			if resp.StatusCode == http.StatusOK {
+				return nil
+			}
+			statusCode = strconv.Itoa(resp.StatusCode)
 		}
 
 		if resp != nil {
 			resp.Body.Close()
 		}
 
-		m.Debug().Msgf("Attempt %d failed: %s", attempt, err)
+		m.Debug().Msgf("Attempt %d failed on %s : status %s err %s", attempt, url, statusCode, err)
 		time.Sleep(1 * time.Second)
 	}
 	return err
diff --git a/internal/app/setup.go b/internal/app/setup.go
index 706fb53..60bbb1d 100644
--- a/internal/app/setup.go
+++ b/internal/app/setup.go
@@ -110,8 +110,13 @@ func (a *App) loadStarlarkConfig(dryRun DryRun) error {
 		return err
 	}
 
+	var stripAppPath bool
+	if stripAppPath, err = a.checkAppPathStripping(); err != nil {
+		return err
+	}
+
 	// Load container config. The proxy config in routes depends on this being loaded first
-	if err = a.loadContainerManager(dryRun); err != nil {
+	if err = a.loadContainerManager(stripAppPath); err != nil {
 		return err
 	}
 
@@ -318,6 +323,63 @@ func verifyConfig(globals starlark.StringDict) (*starlarkstruct.Struct, error) {
 	return appDef, nil
 }
 
+// checkAppPathStripping checks if the app path should be stripped from the request path for container proxying
+// This is required for container health checks.
+func (a *App) checkAppPathStripping() (bool, error) {
+	appPathStripping := true
+	// Iterate through all the routes
+	routes, err := a.appDef.Attr("routes")
+	if err != nil {
+		return false, err
+	}
+
+	var ok bool
+	var routeList *starlark.List
+	if routeList, ok = routes.(*starlark.List); !ok {
+		return false, fmt.Errorf("routes is not a list")
+	}
+
+	iter := routeList.Iterate()
+	var val starlark.Value
+	var count int
+
+	for iter.Next(&val) {
+		count += 1
+		var pageDef *starlarkstruct.Struct
+		if pageDef, ok = val.(*starlarkstruct.Struct); !ok {
+			return false, fmt.Errorf("routes entry %d is not a struct", count)
+		}
+
+		_, err := pageDef.Attr("config")
+		if err == nil {
+			// "config" is defined, this must be a proxy config instead of a page definition
+			var configAttr starlark.HasAttrs
+			if configAttr, err = getProxyConfig(count, pageDef); err != nil {
+				return false, err
+			}
+
+			var urlValue starlark.Value
+			if urlValue, err = configAttr.Attr("Url"); err != nil {
+				return false, err
+			}
+
+			if urlValue.(starlark.String).GoString() != apptype.CONTAINER_URL {
+				// Not proxying to container url, ignore
+				continue
+			}
+
+			var stripAppValue starlark.Value
+			if stripAppValue, err = configAttr.Attr("StripApp"); err != nil {
+				return false, err
+			}
+
+			return bool(stripAppValue.(starlark.Bool)), nil
+		}
+	}
+
+	return appPathStripping, nil
+}
+
 func (a *App) initRouter() error {
 	var defaultHandler starlark.Callable
 	if a.globals.Has(apptype.DEFAULT_HANDLER) {
@@ -488,57 +550,74 @@ func (a *App) addRoute(count int, router *chi.Mux, routeVal starlark.Value, defa
 	return rootWildcard, nil
 }
 
-func (a *App) addProxyConfig(count int, router *chi.Mux, proxyDef *starlarkstruct.Struct) (bool, error) {
+// getProxyConfig extracts the proxy config from the proxy definition
+func getProxyConfig(count int, proxyDef *starlarkstruct.Struct) (starlark.HasAttrs, error) {
 	var err error
 	var pathStr string
-	rootWildcard := false
 
 	if pathStr, err = apptype.GetStringAttr(proxyDef, "path"); err != nil {
-		return rootWildcard, err
-	}
-
-	if pathStr == "/" {
-		rootWildcard = true // Root wildcard path, static files are not served
+		return nil, err
 	}
 
 	var ok bool
 	var responseAttr starlark.HasAttrs
 	pluginResponse, err := proxyDef.Attr("config")
 	if err != nil {
-		return rootWildcard, err
+		return nil, err
 	}
 	if responseAttr, ok = pluginResponse.(starlark.HasAttrs); !ok {
-		return rootWildcard, fmt.Errorf("proxy entry %d:%s is not a proxy response", count, pathStr)
+		return nil, fmt.Errorf("proxy entry %d:%s is not a proxy response", count, pathStr)
 	}
 
 	errorValue, err := responseAttr.Attr("error")
 	if err != nil {
-		return rootWildcard, fmt.Errorf("error in proxy config: %w", err)
+		return nil, fmt.Errorf("error in proxy config: %w", err)
 	}
 
 	if errorValue != nil && errorValue != starlark.None {
 		var errorString starlark.String
 		if errorString, ok = errorValue.(starlark.String); !ok {
-			return rootWildcard, fmt.Errorf("error in proxy config: %w", err)
+			return nil, fmt.Errorf("error in proxy config: %w", err)
 		}
 
 		if errorString.GoString() != "" {
-			return rootWildcard, fmt.Errorf("error in proxy config: %s", errorString.GoString())
+			return nil, fmt.Errorf("error in proxy config: %s", errorString.GoString())
 		}
 	}
 
 	config, err := responseAttr.Attr("value")
 	if err != nil {
-		return rootWildcard, err
+		return nil, err
 	}
 
 	if config.Type() != "ProxyConfig" {
-		return rootWildcard, fmt.Errorf("proxy entry %d:%s is not a proxy config", count, pathStr)
+		return nil, fmt.Errorf("proxy entry %d:%s is not a proxy config", count, pathStr)
 	}
 
 	var configAttr starlark.HasAttrs
 	if configAttr, ok = config.(starlark.HasAttrs); !ok {
-		return rootWildcard, fmt.Errorf("proxy entry %d:%s is not a proxy config attr", count, pathStr)
+		return nil, fmt.Errorf("proxy entry %d:%s is not a proxy config attr", count, pathStr)
+	}
+
+	return configAttr, nil
+}
+
+func (a *App) addProxyConfig(count int, router *chi.Mux, proxyDef *starlarkstruct.Struct) (bool, error) {
+	var err error
+	var pathStr string
+	rootWildcard := false
+
+	if pathStr, err = apptype.GetStringAttr(proxyDef, "path"); err != nil {
+		return rootWildcard, err
+	}
+
+	if pathStr == "/" {
+		rootWildcard = true // Root wildcard path, static files are not served
+	}
+
+	var configAttr starlark.HasAttrs
+	if configAttr, err = getProxyConfig(count, proxyDef); err != nil {
+		return rootWildcard, err
 	}
 
 	var urlValue, stripPathValue starlark.Value
diff --git a/internal/types/types.go b/internal/types/types.go
index 4bfaa02..190b8b6 100644
--- a/internal/types/types.go
+++ b/internal/types/types.go
@@ -262,8 +262,8 @@ type VersionMetadata struct {
 type AppEntry struct {
 	Id         AppId       `json:"id"`
 	Path       string      `json:"path"`
-	MainApp    AppId       `json:"main_app"` // the id of the app that this app is linked to
 	Domain     string      `json:"domain"`
+	MainApp    AppId       `json:"main_app"` // the id of the app that this app is linked to
 	SourceUrl  string      `json:"source_url"`
 	IsDev      bool        `json:"is_dev"`
 	UserID     string      `json:"user_id"`