diff --git a/components/gitpod-cli/cmd/rebuild.go b/components/gitpod-cli/cmd/rebuild.go
index ee575297607453..c4a059f7b572dd 100644
--- a/components/gitpod-cli/cmd/rebuild.go
+++ b/components/gitpod-cli/cmd/rebuild.go
@@ -238,6 +238,9 @@ func runRebuild(ctx context.Context, supervisorClient *supervisor.SupervisorClie
 	for _, env := range debugEnvs.Envs {
 		envs += env + "\n"
 	}
+	for _, env := range rebuildOpts.GitpodEnvs {
+		envs += env + "\n"
+	}
 	for _, env := range workspaceEnvs {
 		envs += fmt.Sprintf("%s=%s\n", env.Name, env.Value)
 	}
@@ -432,6 +435,9 @@ var rebuildOpts struct {
 	LogLevel        string
 	From            string
 	Prebuild        bool
+
+	// internal
+	GitpodEnvs []string
 }
 
 var rebuildCmd = &cobra.Command{
@@ -467,4 +473,8 @@ func init() {
 	rebuildCmd.PersistentFlags().StringVarP(&rebuildOpts.LogLevel, "log", "", "error", "Log level to use. Allowed values are 'error', 'warn', 'info', 'debug', 'trace'.")
 	rebuildCmd.PersistentFlags().StringVarP(&rebuildOpts.From, "from", "", "", "Starts from 'prebuild' or 'snapshot'.")
 	rebuildCmd.PersistentFlags().BoolVarP(&rebuildOpts.Prebuild, "prebuild", "", false, "starts as a prebuild workspace (--from is ignored).")
+
+	// internal
+	rebuildCmd.PersistentFlags().StringArrayVarP(&rebuildOpts.GitpodEnvs, "gitpod-env", "", nil, "")
+	rebuildCmd.PersistentFlags().MarkHidden("gitpod-env")
 }
diff --git a/components/gitpod-cli/rebuild.sh b/components/gitpod-cli/rebuild.sh
new file mode 100755
index 00000000000000..56d6d0dc99d964
--- /dev/null
+++ b/components/gitpod-cli/rebuild.sh
@@ -0,0 +1,18 @@
+#!/bin/bash
+# Copyright (c) 2023 Gitpod GmbH. All rights reserved.
+# Licensed under the GNU Affero General Public License (AGPL).
+# See License.AGPL.txt in the project root for license information.
+
+set -Eeuo pipefail
+
+DIR="$(dirname "$(realpath "$0")")"
+COMPONENT="$(basename "$DIR")"
+cd "$DIR"
+
+# build
+go build .
+echo "$COMPONENT built"
+
+sudo rm -rf "/.supervisor/$COMPONENT" && true
+sudo mv ./"$COMPONENT" /.supervisor
+echo "$COMPONENT in /.supervisor replaced"
diff --git a/components/supervisor/.vscode/launch.json b/components/supervisor/.vscode/launch.json
new file mode 100644
index 00000000000000..b3662ad4dbbd31
--- /dev/null
+++ b/components/supervisor/.vscode/launch.json
@@ -0,0 +1,14 @@
+{
+    "version": "0.2.0",
+    "configurations": [
+        {
+            "name": "Attach to Process",
+            "type": "go",
+            "request": "attach",
+            "mode": "local",
+            "asRoot": true,
+            "console": "integratedTerminal",
+            "processId": "supervisor"
+        }
+    ]
+}
diff --git a/components/supervisor/pkg/config/gitpod-config.go b/components/supervisor/pkg/config/gitpod-config.go
index 6c73f5cc64e39f..447eefd2288961 100644
--- a/components/supervisor/pkg/config/gitpod-config.go
+++ b/components/supervisor/pkg/config/gitpod-config.go
@@ -7,13 +7,14 @@ package config
 import (
 	"context"
 	"os"
+	"path/filepath"
 	"sync"
 	"time"
 
 	"github.com/fsnotify/fsnotify"
-	"github.com/sirupsen/logrus"
-	"gopkg.in/yaml.v2"
+	"gopkg.in/yaml.v3"
 
+	"github.com/gitpod-io/gitpod/common-go/log"
 	gitpod "github.com/gitpod-io/gitpod/gitpod-protocol"
 )
 
@@ -23,19 +24,111 @@ type ConfigInterface interface {
 	Watch(ctx context.Context)
 	// Observe provides channels triggered whenever the config is changed
 	Observe(ctx context.Context) <-chan *gitpod.GitpodConfig
+	// Observe provides channels triggered whenever the image file is changed
+	ObserveImageFile(ctx context.Context) <-chan *struct{}
 }
 
 // ConfigService provides access to the gitpod config file.
 type ConfigService struct {
-	location      string
 	locationReady <-chan struct{}
 
-	cond   *sync.Cond
-	config *gitpod.GitpodConfig
+	configLocation string
+	configWatcher  *fileWatcher[gitpod.GitpodConfig]
 
-	pollTimer *time.Timer
+	imageWatcher *fileWatcher[struct{}]
+}
 
-	log *logrus.Entry
+// NewConfigService creates a new instance of ConfigService.
+func NewConfigService(configLocation string, locationReady <-chan struct{}) *ConfigService {
+	return &ConfigService{
+		locationReady:  locationReady,
+		configLocation: configLocation,
+		configWatcher: newFileWatcher(func(data []byte) (*gitpod.GitpodConfig, error) {
+			var config *gitpod.GitpodConfig
+			err := yaml.Unmarshal(data, &config)
+			return config, err
+		}),
+		imageWatcher: newFileWatcher(func(data []byte) (*struct{}, error) {
+			return &struct{}{}, nil
+		}),
+	}
+}
+
+// Observe provides channels triggered whenever the config is changed.
+func (service *ConfigService) Observe(ctx context.Context) <-chan *gitpod.GitpodConfig {
+	return service.configWatcher.observe(ctx)
+}
+
+// Observe provides channels triggered whenever the image file is changed
+func (service *ConfigService) ObserveImageFile(ctx context.Context) <-chan *struct{} {
+	return service.imageWatcher.observe(ctx)
+}
+
+// Watch starts the config watching.
+func (service *ConfigService) Watch(ctx context.Context) {
+	select {
+	case <-service.locationReady:
+	case <-ctx.Done():
+		return
+	}
+	go service.watchImageFile(ctx)
+	service.configWatcher.watch(ctx, service.configLocation)
+}
+
+func (service *ConfigService) watchImageFile(ctx context.Context) {
+	var (
+		imageLocation string
+		cancelWatch   func()
+	)
+	defer func() {
+		if cancelWatch != nil {
+			cancelWatch()
+		}
+	}()
+	cfgs := service.configWatcher.observe(ctx)
+	for {
+		select {
+		case cfg, ok := <-cfgs:
+			if !ok {
+				return
+			}
+			var currentImageLocation string
+			if cfg != nil {
+				switch img := cfg.Image.(type) {
+				case map[string]interface{}:
+					if file, ok := img["file"].(string); ok {
+						currentImageLocation = filepath.Join(filepath.Dir(service.configLocation), file)
+					}
+				}
+			}
+			if imageLocation == currentImageLocation {
+				continue
+			}
+			if cancelWatch != nil {
+				cancelWatch()
+				cancelWatch = nil
+				service.imageWatcher.reset()
+			}
+			imageLocation = currentImageLocation
+			if imageLocation == "" {
+				continue
+			}
+			watchCtx, cancel := context.WithCancel(ctx)
+			cancelWatch = cancel
+			go service.imageWatcher.watch(watchCtx, imageLocation)
+		case <-ctx.Done():
+			return
+		}
+	}
+}
+
+type fileWatcher[T any] struct {
+	unmarshal func(data []byte) (*T, error)
+
+	cond *sync.Cond
+	data *T
+
+	pollTimer *time.Timer
 
 	ready     chan struct{}
 	readyOnce sync.Once
@@ -43,30 +136,26 @@ type ConfigService struct {
 	debounceDuration time.Duration
 }
 
-// NewConfigService creates a new instance of ConfigService.
-func NewConfigService(configLocation string, locationReady <-chan struct{}, log *logrus.Entry) *ConfigService {
-	return &ConfigService{
-		location:         configLocation,
-		locationReady:    locationReady,
+func newFileWatcher[T any](unmarshal func(data []byte) (*T, error)) *fileWatcher[T] {
+	return &fileWatcher[T]{
+		unmarshal:        unmarshal,
 		cond:             sync.NewCond(&sync.Mutex{}),
-		log:              log.WithField("location", configLocation),
 		ready:            make(chan struct{}),
 		debounceDuration: 100 * time.Millisecond,
 	}
 }
 
-// Observe provides channels triggered whenever the config is changed.
-func (service *ConfigService) Observe(ctx context.Context) <-chan *gitpod.GitpodConfig {
-	configs := make(chan *gitpod.GitpodConfig)
+func (service *fileWatcher[T]) observe(ctx context.Context) <-chan *T {
+	results := make(chan *T)
 	go func() {
-		defer close(configs)
+		defer close(results)
 
 		<-service.ready
 
 		service.cond.L.Lock()
 		defer service.cond.L.Unlock()
 		for {
-			configs <- service.config
+			results <- service.data
 
 			service.cond.Wait()
 			if ctx.Err() != nil {
@@ -74,58 +163,62 @@ func (service *ConfigService) Observe(ctx context.Context) <-chan *gitpod.Gitpod
 			}
 		}
 	}()
-	return configs
+	return results
 }
 
-// Watch starts the config watching.
-func (service *ConfigService) Watch(ctx context.Context) {
-	service.log.Info("gitpod config watcher: starting...")
+func (service *fileWatcher[T]) markReady() {
+	service.readyOnce.Do(func() {
+		close(service.ready)
+	})
+}
 
-	select {
-	case <-service.locationReady:
-	case <-ctx.Done():
-		return
-	}
+func (service *fileWatcher[T]) reset() {
+	service.cond.L.Lock()
+	defer service.cond.L.Unlock()
 
-	_, err := os.Stat(service.location)
-	if os.IsNotExist(err) {
-		service.poll(ctx)
+	if service.data != nil {
+		service.data = nil
+		service.cond.Broadcast()
 	}
-	service.watch(ctx)
 }
 
-func (service *ConfigService) markReady() {
-	service.readyOnce.Do(func() {
-		close(service.ready)
-	})
+func (service *fileWatcher[T]) watch(ctx context.Context, location string) {
+	log.WithField("location", location).Info("file watcher: starting...")
+
+	_, err := os.Stat(location)
+	if os.IsNotExist(err) {
+		service.poll(ctx, location)
+	} else {
+		service.doWatch(ctx, location)
+	}
 }
 
-func (service *ConfigService) watch(ctx context.Context) {
+func (service *fileWatcher[T]) doWatch(ctx context.Context, location string) {
 	watcher, err := fsnotify.NewWatcher()
 	defer func() {
 		if err != nil {
-			service.log.WithError(err).Error("gitpod config watcher: failed to start")
+			log.WithField("location", location).WithError(err).Error("file watcher: failed to start")
 			return
 		}
 
-		service.log.Info("gitpod config watcher: started")
+		log.WithField("location", location).Info("file watcher: started")
 	}()
 	if err != nil {
 		return
 	}
 
-	err = watcher.Add(service.location)
+	err = watcher.Add(location)
 	if err != nil {
 		watcher.Close()
 		return
 	}
 
 	go func() {
-		defer service.log.Info("gitpod config watcher: stopped")
+		defer log.WithField("location", location).Info("file watcher: stopped")
 		defer watcher.Close()
 
 		polling := make(chan struct{}, 1)
-		service.scheduleUpdateConfig(ctx, polling)
+		service.scheduleUpdate(ctx, polling, location)
 		for {
 			select {
 			case <-polling:
@@ -133,32 +226,32 @@ func (service *ConfigService) watch(ctx context.Context) {
 			case <-ctx.Done():
 				return
 			case err := <-watcher.Errors:
-				service.log.WithError(err).Error("gitpod config watcher: failed to watch")
+				log.WithField("location", location).WithError(err).Error("file watcher: failed to watch")
 			case <-watcher.Events:
-				service.scheduleUpdateConfig(ctx, polling)
+				service.scheduleUpdate(ctx, polling, location)
 			}
 		}
 	}()
 }
 
-func (service *ConfigService) scheduleUpdateConfig(ctx context.Context, polling chan<- struct{}) {
+func (service *fileWatcher[T]) scheduleUpdate(ctx context.Context, polling chan<- struct{}, location string) {
 	service.cond.L.Lock()
 	defer service.cond.L.Unlock()
 	if service.pollTimer != nil {
 		service.pollTimer.Stop()
 	}
 	service.pollTimer = time.AfterFunc(service.debounceDuration, func() {
-		err := service.updateConfig()
+		err := service.update(location)
 		if os.IsNotExist(err) {
 			polling <- struct{}{}
-			go service.poll(ctx)
+			go service.poll(ctx, location)
 		} else if err != nil {
-			service.log.WithError(err).Error("gitpod config watcher: failed to parse")
+			log.WithField("location", location).WithError(err).Error("file watcher: failed to parse")
 		}
 	})
 }
 
-func (service *ConfigService) poll(ctx context.Context) {
+func (service *fileWatcher[T]) poll(ctx context.Context, location string) {
 	service.markReady()
 
 	timer := time.NewTicker(2 * time.Second)
@@ -171,35 +264,33 @@ func (service *ConfigService) poll(ctx context.Context) {
 		case <-timer.C:
 		}
 
-		if _, err := os.Stat(service.location); !os.IsNotExist(err) {
-			service.watch(ctx)
+		if _, err := os.Stat(location); !os.IsNotExist(err) {
+			service.doWatch(ctx, location)
 			return
 		}
 	}
 }
 
-func (service *ConfigService) updateConfig() error {
+func (service *fileWatcher[T]) update(location string) error {
 	service.cond.L.Lock()
 	defer service.cond.L.Unlock()
 
-	config, err := service.parse()
+	data, err := service.parse(location)
 	if err == nil || os.IsNotExist(err) {
-		service.config = config
+		service.data = data
 		service.markReady()
 		service.cond.Broadcast()
 
-		service.log.WithField("config", service.config).Debug("gitpod config watcher: updated")
+		log.WithField("location", location).WithField("data", service.data).Debug("file watcher: updated")
 	}
 
 	return err
 }
 
-func (service *ConfigService) parse() (*gitpod.GitpodConfig, error) {
-	data, err := os.ReadFile(service.location)
+func (service *fileWatcher[T]) parse(location string) (*T, error) {
+	data, err := os.ReadFile(location)
 	if err != nil {
 		return nil, err
 	}
-	var config *gitpod.GitpodConfig
-	err = yaml.Unmarshal(data, &config)
-	return config, err
+	return service.unmarshal(data)
 }
diff --git a/components/supervisor/pkg/config/gitpod-config_analytics_test.go b/components/supervisor/pkg/config/gitpod-config_analytics_test.go
index bf7f5b3934dad8..c7f31679b85720 100644
--- a/components/supervisor/pkg/config/gitpod-config_analytics_test.go
+++ b/components/supervisor/pkg/config/gitpod-config_analytics_test.go
@@ -10,6 +10,7 @@ import (
 
 	"github.com/google/go-cmp/cmp"
 
+	"github.com/gitpod-io/gitpod/common-go/log"
 	gitpod "github.com/gitpod-io/gitpod/gitpod-protocol"
 )
 
@@ -65,7 +66,7 @@ func TestAnalyzeGitpodConfig(t *testing.T) {
 	for _, test := range tests {
 		t.Run(test.Desc, func(t *testing.T) {
 			var fields []string
-			analyzer := NewConfigAnalyzer(log, 100*time.Millisecond, func(field string) {
+			analyzer := NewConfigAnalyzer(log.Log, 100*time.Millisecond, func(field string) {
 				fields = append(fields, field)
 			}, test.Prev)
 			<-analyzer.Analyse(test.Current)
diff --git a/components/supervisor/pkg/config/gitpod-config_test.go b/components/supervisor/pkg/config/gitpod-config_test.go
index 60b8b9b9e35a40..06ae768a78f7f2 100644
--- a/components/supervisor/pkg/config/gitpod-config_test.go
+++ b/components/supervisor/pkg/config/gitpod-config_test.go
@@ -12,14 +12,11 @@ import (
 	"time"
 
 	"github.com/google/go-cmp/cmp"
-	"github.com/sirupsen/logrus"
 	"golang.org/x/sync/errgroup"
 
 	gitpod "github.com/gitpod-io/gitpod/gitpod-protocol"
 )
 
-var log = logrus.NewEntry(logrus.StandardLogger())
-
 func TestGitpodConfig(t *testing.T) {
 	tests := []struct {
 		Desc        string
@@ -89,7 +86,7 @@ vscode:
 			defer os.RemoveAll(tempDir)
 
 			locationReady := make(chan struct{})
-			configService := NewConfigService(tempDir+"/.gitpod.yml", locationReady, log)
+			configService := NewConfigService(tempDir+"/.gitpod.yml", locationReady)
 			ctx, cancel := context.WithCancel(context.Background())
 			defer cancel()
 			close(locationReady)
@@ -118,7 +115,7 @@ vscode:
 					t.Fatal(err)
 				}
 
-				err = os.WriteFile(configService.location, []byte(test.Content), 0o600)
+				err = os.WriteFile(configService.configLocation, []byte(test.Content), 0o600)
 				if err != nil {
 					t.Fatal(err)
 				}
@@ -139,7 +136,7 @@ vscode:
 					t.Fatal(err)
 				}
 
-				err = os.Remove(configService.location)
+				err = os.Remove(configService.configLocation)
 				if err != nil {
 					t.Fatal(err)
 				}
@@ -156,7 +153,7 @@ func TestInvalidGitpodConfig(t *testing.T) {
 	defer os.RemoveAll(tempDir)
 
 	locationReady := make(chan struct{})
-	configService := NewConfigService(tempDir+"/.gitpod.yml", locationReady, log)
+	configService := NewConfigService(tempDir+"/.gitpod.yml", locationReady)
 	ctx, cancel := context.WithCancel(context.Background())
 	defer cancel()
 	close(locationReady)
@@ -170,7 +167,7 @@ func TestInvalidGitpodConfig(t *testing.T) {
 		t.Errorf("unexpected output (-want +got):\n%s", diff)
 	}
 
-	err = os.WriteFile(configService.location, []byte(`
+	err = os.WriteFile(configService.configLocation, []byte(`
 ports:
   - port: 8080
 
@@ -194,7 +191,7 @@ vscode:
 		t.Errorf("unexpected output (-want +got):\n%s", diff)
 	}
 
-	err = os.WriteFile(configService.location, []byte(`
+	err = os.WriteFile(configService.configLocation, []byte(`
 ports:
   - port:
 	visibility: private
@@ -212,9 +209,9 @@ vscode:
 		t.Fatal(err)
 	}
 
-	time.Sleep(configService.debounceDuration * 10)
+	time.Sleep(configService.configWatcher.debounceDuration * 10)
 
-	err = os.WriteFile(configService.location, []byte(`
+	err = os.WriteFile(configService.configLocation, []byte(`
 ports:
   - port: 8081
 `), 0o600)
@@ -229,3 +226,84 @@ ports:
 		t.Errorf("unexpected output (-want +got):\n%s", diff)
 	}
 }
+
+func TestWatchImageFile(t *testing.T) {
+	tempDir, err := os.MkdirTemp("", "test-gitpod-config-*")
+	if err != nil {
+		t.Fatal(err)
+	}
+	defer os.RemoveAll(tempDir)
+
+	locationReady := make(chan struct{})
+	configService := NewConfigService(tempDir+"/.gitpod.yml", locationReady)
+	ctx, cancel := context.WithCancel(context.Background())
+	defer cancel()
+	close(locationReady)
+
+	go configService.Watch(ctx)
+
+	listener := configService.ObserveImageFile(ctx)
+
+	err = os.WriteFile(configService.configLocation, []byte(`
+image:
+  file: Dockerfile
+`), 0o600)
+	if err != nil {
+		t.Fatal(err)
+	}
+
+	changes := <-listener
+	if diff := cmp.Diff((*struct{})(nil), changes); diff != "" {
+		t.Errorf("unexpected output (-want +got):\n%s", diff)
+	}
+
+	imageLocation := tempDir + "/Dockerfile"
+	err = os.WriteFile(imageLocation, []byte(`
+FROM ubuntu
+`), 0o600)
+	if err != nil {
+		t.Fatal(err)
+	}
+
+	changes = <-listener
+	if diff := cmp.Diff(&struct{}{}, changes); diff != "" {
+		t.Errorf("unexpected output (-want +got):\n%s", diff)
+	}
+
+	err = os.WriteFile(configService.configLocation, []byte(`
+image: ubuntu
+`), 0o600)
+	if err != nil {
+		t.Fatal(err)
+	}
+
+	changes = <-listener
+	if diff := cmp.Diff((*struct{})(nil), changes); diff != "" {
+		t.Errorf("unexpected output (-want +got):\n%s", diff)
+	}
+
+	err = os.WriteFile(configService.configLocation, []byte(`
+image:
+  file: Dockerfile
+`), 0o600)
+	if err != nil {
+		t.Fatal(err)
+	}
+
+	changes = <-listener
+	if diff := cmp.Diff(&struct{}{}, changes); diff != "" {
+		t.Errorf("unexpected output (-want +got):\n%s", diff)
+	}
+
+	err = os.WriteFile(imageLocation, []byte(`
+FROM node
+`), 0o600)
+	if err != nil {
+		t.Fatal(err)
+	}
+
+	changes = <-listener
+	if diff := cmp.Diff(&struct{}{}, changes); diff != "" {
+		t.Errorf("unexpected output (-want +got):\n%s", diff)
+	}
+}
diff --git a/components/supervisor/pkg/ports/ports-config_test.go b/components/supervisor/pkg/ports/ports-config_test.go
index 43fe8f34ec721c..d8437f74cbabac 100644
--- a/components/supervisor/pkg/ports/ports-config_test.go
+++ b/components/supervisor/pkg/ports/ports-config_test.go
@@ -83,8 +83,10 @@ func TestPortsConfig(t *testing.T) {
 		t.Run(test.Desc, func(t *testing.T) {
 			configService := &testGitpodConfigService{
 				configs: make(chan *gitpod.GitpodConfig),
+				changes: make(chan *struct{}),
 			}
 			defer close(configService.configs)
+			defer close(configService.changes)
 
 			context, cancel := context.WithCancel(context.Background())
 			defer cancel()
@@ -128,6 +130,7 @@ type PortConfigTestExpectations struct {
 
 type testGitpodConfigService struct {
 	configs chan *gitpod.GitpodConfig
+	changes chan *struct{}
 }
 
 func (service *testGitpodConfigService) Watch(ctx context.Context) {
@@ -136,3 +139,7 @@ func (service *testGitpodConfigService) Watch(ctx context.Context) {
 func (service *testGitpodConfigService) Observe(ctx context.Context) <-chan *gitpod.GitpodConfig {
 	return service.configs
 }
+
+func (service *testGitpodConfigService) ObserveImageFile(ctx context.Context) <-chan *struct{} {
+	return service.changes
+}
diff --git a/components/supervisor/pkg/supervisor/supervisor.go b/components/supervisor/pkg/supervisor/supervisor.go
index f15ea619876784..a2287e29653317 100644
--- a/components/supervisor/pkg/supervisor/supervisor.go
+++ b/components/supervisor/pkg/supervisor/supervisor.go
@@ -273,7 +273,7 @@ func Run(options ...RunOption) {
 	}
 	tokenService.provider[KindGit] = []tokenProvider{NewGitTokenProvider(gitpodService, cfg.WorkspaceConfig, notificationService)}
 
-	gitpodConfigService := config.NewConfigService(cfg.RepoRoot+"/.gitpod.yml", cstate.ContentReady(), log.Log)
+	gitpodConfigService := config.NewConfigService(cfg.RepoRoot+"/.gitpod.yml", cstate.ContentReady())
 	go gitpodConfigService.Watch(ctx)
 
 	var exposedPorts ports.ExposedPortsInterface
@@ -297,7 +297,7 @@ func Run(options ...RunOption) {
 		topService.Observe(ctx)
 	}
 
-	if !cfg.isHeadless() && !opts.RunGP && !cfg.isDebugWorkspace() {
+	if !cfg.isHeadless() && !opts.RunGP {
 		go analyseConfigChanges(ctx, cfg, telemetry, gitpodConfigService)
 		go analysePerfChanges(ctx, cfg, telemetry, topService)
 	}
@@ -1592,17 +1592,20 @@ func analysePerfChanges(ctx context.Context, wscfg *Config, w analytics.Writer,
 		if !analyzer.analyze(used) {
 			return
 		}
-		log.WithField("buckets", analyzer.buckets).WithField("used", used).WithField("label", analyzer.label).Debug("gitpod perf analytics: changed")
-		w.Track(analytics.TrackMessage{
-			Identity: analytics.Identity{UserID: wscfg.OwnerId},
-			Event:    "gitpod_" + analyzer.label + "_changed",
-			Properties: map[string]interface{}{
-				"used":        used,
-				"buckets":     analyzer.buckets,
-				"instanceId":  wscfg.WorkspaceInstanceID,
-				"workspaceId": wscfg.WorkspaceID,
-			},
-		})
+		if wscfg.isDebugWorkspace() {
+			log.WithField("buckets", analyzer.buckets).WithField("used", used).WithField("label", analyzer.label).Info("gitpod perf analytics: changed")
+		} else {
+			w.Track(analytics.TrackMessage{
+				Identity: analytics.Identity{UserID: wscfg.OwnerId},
+				Event:    "gitpod_" + analyzer.label + "_changed",
+				Properties: map[string]interface{}{
+					"used":        used,
+					"buckets":     analyzer.buckets,
+					"instanceId":  wscfg.WorkspaceInstanceID,
+					"workspaceId": wscfg.WorkspaceID,
+				},
+			})
+		}
 	}
 
 	cpuAnalyzer := &PerfAnalyzer{label: "cpu", defs: []int{1, 2, 3, 4, 5, 6, 7, 8}}
@@ -1623,10 +1626,64 @@ func analysePerfChanges(ctx context.Context, wscfg *Config, w analytics.Writer,
 	}
 }
 
+func analyzeImageFileChanges(ctx context.Context, wscfg *Config, w analytics.Writer, cfgobs config.ConfigInterface, debounceDuration time.Duration) {
+	var (
+		timer *time.Timer
+		mu    sync.Mutex
+	)
+	analyze := func(change *struct{}) {
+		mu.Lock()
+		defer mu.Unlock()
+		if timer != nil && !timer.Stop() {
+			<-timer.C
+		}
+		timer = time.AfterFunc(debounceDuration, func() {
+			mu.Lock()
+			defer mu.Unlock()
+			timer = nil
+			msg := analytics.TrackMessage{
+				Identity: analytics.Identity{UserID: wscfg.OwnerId},
+				Event:    "gitpod_image_file_changed",
+				Properties: map[string]interface{}{
+					"instanceId":  wscfg.WorkspaceInstanceID,
+					"workspaceId": wscfg.WorkspaceID,
+					"exists":      change != nil,
+				},
+			}
+			if !wscfg.isDebugWorkspace() {
+				w.Track(msg)
+			} else {
+				log.WithField("msg", msg).Info("gitpod config analytics: image file changed")
+			}
+		})
+	}
+	changes := cfgobs.ObserveImageFile(ctx)
+	initial := true
+	for {
+		select {
+		case change, ok := <-changes:
+			if !ok {
+				return
+			}
+			if initial {
+				// only report changes, not initial state
+				initial = false
+			} else {
+				analyze(change)
+			}
+		case <-ctx.Done():
+			return
+		}
+	}
+}
+
 func analyseConfigChanges(ctx context.Context, wscfg *Config, w analytics.Writer, cfgobs config.ConfigInterface) {
 	var analyzer *config.ConfigAnalyzer
 	log.Debug("gitpod config analytics: watching...")
 
+	debounceDuration := 5 * time.Second
+	go analyzeImageFileChanges(ctx, wscfg, w, cfgobs, debounceDuration)
+
 	cfgs := cfgobs.Observe(ctx)
 	for {
 		select {
@@ -1637,8 +1694,8 @@ func analyseConfigChanges(ctx context.Context, wscfg *Config, w analytics.Writer
 			if analyzer != nil {
 				analyzer.Analyse(cfg)
 			} else {
-				analyzer = config.NewConfigAnalyzer(log.Log, 5*time.Second, func(field string) {
-					w.Track(analytics.TrackMessage{
+				analyzer = config.NewConfigAnalyzer(log.Log, debounceDuration, func(field string) {
+					msg := analytics.TrackMessage{
 						Identity: analytics.Identity{UserID: wscfg.OwnerId},
 						Event:    "gitpod_config_changed",
 						Properties: map[string]interface{}{
@@ -1646,7 +1703,12 @@ func analyseConfigChanges(ctx context.Context, wscfg *Config, w analytics.Writer
 							"instanceId":  wscfg.WorkspaceInstanceID,
 							"workspaceId": wscfg.WorkspaceID,
 						},
-					})
+					}
+					if !wscfg.isDebugWorkspace() {
+						w.Track(msg)
+					} else {
+						log.WithField("msg", msg).Info("gitpod config analytics: config changed")
+					}
 				}, cfg)
 			}
 
diff --git a/components/supervisor/validate.sh b/components/supervisor/validate.sh
new file mode 100755
index 00000000000000..fe3652d121e61c
--- /dev/null
+++ b/components/supervisor/validate.sh
@@ -0,0 +1,23 @@
+#!/bin/bash
+# Copyright (c) 2023 Gitpod GmbH. All rights reserved.
+# Licensed under the GNU Affero General Public License (AGPL).
+# See License.AGPL.txt in the project root for license information.
+
+set -Eeuo pipefail
+
+ROOT_DIR="$(realpath "$(dirname "$0")/../..")"
+bash "$ROOT_DIR/components/gitpod-cli/rebuild.sh"
+
+DIR="$(dirname "$(realpath "$0")")"
+COMPONENT="$(basename "$DIR")"
+cd "$DIR"
+
+# build
+go build -gcflags=all="-N -l" .
+echo "$COMPONENT built"
+
+sudo rm -rf "/.supervisor/$COMPONENT" && true
+sudo mv ./"$COMPONENT" /.supervisor
+echo "$COMPONENT in /.supervisor replaced"
+
+gp rebuild --workspace-folder="$ROOT_DIR/dev/ide/example/workspace" --gitpod-env "GITPOD_ANALYTICS_SEGMENT_KEY=YErmvd89wPsrCuGcVnF2XAl846W9WIGl" "$@"
diff --git a/dev/ide/example/workspace/.gitpod.yml b/dev/ide/example/workspace/.gitpod.yml
new file mode 100644
index 00000000000000..5ce220c1c14804
--- /dev/null
+++ b/dev/ide/example/workspace/.gitpod.yml
@@ -0,0 +1,2 @@
+image:
+  file: Dockerfile
diff --git a/dev/ide/example/workspace/Dockerfile b/dev/ide/example/workspace/Dockerfile
new file mode 100644
index 00000000000000..c79638293fbd98
--- /dev/null
+++ b/dev/ide/example/workspace/Dockerfile
@@ -0,0 +1,3 @@
+FROM ubuntu
+
+RUN apt-get update -y && apt-get install -y git sudo curl