diff --git a/agent/assistant/sandbox_v2.go b/agent/assistant/sandbox_v2.go
index a8026ae9..5214ade3 100644
--- a/agent/assistant/sandbox_v2.go
+++ b/agent/assistant/sandbox_v2.go
@@ -48,7 +48,10 @@ func (ast *Assistant) initSandboxV2(ctx *context.Context, opts *context.Options)
 		return nil, nil, nil, "", fmt.Errorf("get connector: %w", err)
 	}
 
-	// 2. Obtain Computer (passes connector for OPENAI_PROXY_* env injection).
+	// 2. Build human-readable DisplayName from real Agent name + Workspace name.
+	cfg.DisplayName = buildBoxDisplayName(ctx, ast.ID, ast.Name)
+
+	// 3. Obtain Computer (passes connector for OPENAI_PROXY_* env injection).
 	computer, identifier, err := sandboxv2.GetComputer(ctx, cfg, manager, conn)
 	if err != nil {
 		closeLoadingV2(ctx, loadingMsgID, "sandbox.failed")
@@ -56,7 +59,7 @@ func (ast *Assistant) initSandboxV2(ctx *context.Context, opts *context.Options)
 	}
 	_ = identifier
 
-	// 3. Get Runner.
+	// 4. Get Runner.
 	runner, err := sandboxv2.Get(cfg.Runner.Name)
 	if err != nil {
 		sandboxv2.LifecycleAction(stdCtx, cfg, computer, manager)
@@ -64,7 +67,7 @@ func (ast *Assistant) initSandboxV2(ctx *context.Context, opts *context.Options)
 		return nil, nil, nil, "", fmt.Errorf("get runner %q: %w", cfg.Runner.Name, err)
 	}
 
-	// 4. Resolve skills directory.
+	// 5. Resolve skills directory.
 	skillsDir := ""
 	if ast.Path != "" {
 		dir := filepath.Join(config.Conf.AppSource, ast.Path, "skills")
@@ -73,7 +76,7 @@ func (ast *Assistant) initSandboxV2(ctx *context.Context, opts *context.Options)
 		}
 	}
 
-	// 5. Convert MCP servers.
+	// 6. Convert MCP servers.
 	var mcpServers []sandboxTypes.MCPServer
 	if ast.MCP != nil {
 		for _, s := range ast.MCP.Servers {
@@ -85,7 +88,7 @@ func (ast *Assistant) initSandboxV2(ctx *context.Context, opts *context.Options)
 		}
 	}
 
-	// 6. Runner.Prepare (standard context).
+	// 7. Runner.Prepare (standard context).
 	err = runner.Prepare(stdCtx, &sandboxTypes.PrepareRequest{
 		Computer:   computer,
 		Config:     cfg,
@@ -199,6 +202,34 @@ func (ast *Assistant) initStandaloneWorkspace(ctx *context.Context) {
 	ctx.SetWorkspace(wsFS)
 }
 
+// buildBoxDisplayName constructs a human-readable display name for a Box
+// using the locale-resolved Agent name and Workspace name (matching the UI list pages).
+func buildBoxDisplayName(ctx *context.Context, assistantID, rawName string) string {
+	agentName := i18n.Tr(assistantID, ctx.Locale, rawName)
+
+	wsName := ""
+	if ctx.Metadata != nil {
+		if wsID, ok := ctx.Metadata["workspace_id"].(string); ok && wsID != "" {
+			if wsm := workspace.M(); wsm != nil {
+				if ws, err := wsm.Get(ctx.Context, wsID); err == nil && ws != nil {
+					wsName = ws.Name
+				}
+			}
+		}
+	}
+
+	if agentName != "" && wsName != "" {
+		return agentName + " / " + wsName
+	}
+	if agentName != "" {
+		return agentName
+	}
+	if wsName != "" {
+		return wsName
+	}
+	return ""
+}
+
 func closeLoadingV2(ctx *context.Context, loadingMsgID, msgKey string) {
 	if loadingMsgID == "" || ctx == nil {
 		return
diff --git a/agent/sandbox/v2/lifecycle.go b/agent/sandbox/v2/lifecycle.go
index d2f28800..bad0b57c 100644
--- a/agent/sandbox/v2/lifecycle.go
+++ b/agent/sandbox/v2/lifecycle.go
@@ -17,7 +17,7 @@ import (
 
 // BuildIdentifier determines the Computer identifier based on lifecycle policy
 // and optional metadata override. Returns "" for oneshot (always new).
-func BuildIdentifier(cfg *types.SandboxConfig, ownerID, chatID, assistantID string, metadata map[string]any) string {
+func BuildIdentifier(cfg *types.SandboxConfig, ownerID, chatID, assistantID, workspaceID string, metadata map[string]any) string {
 	if cfg.Lifecycle == "oneshot" {
 		return ""
 	}
@@ -25,7 +25,7 @@ func BuildIdentifier(cfg *types.SandboxConfig, ownerID, chatID, assistantID stri
 	// Custom identifier from metadata takes precedence.
 	if metadata != nil {
 		if cid, ok := metadata["computer_id"].(string); ok && cid != "" {
-			return fmt.Sprintf("%s-%s", ownerID, cid)
+			return fmt.Sprintf("%s-%s.%s", ownerID, cid, workspaceID)
 		}
 	}
 
@@ -33,7 +33,7 @@ func BuildIdentifier(cfg *types.SandboxConfig, ownerID, chatID, assistantID stri
 	case "session":
 		return fmt.Sprintf("%s-%s", ownerID, chatID)
 	case "longrunning", "persistent":
-		return fmt.Sprintf("%s-%s", ownerID, assistantID)
+		return fmt.Sprintf("%s-%s.%s", ownerID, assistantID, workspaceID)
 	default:
 		return ""
 	}
@@ -44,11 +44,6 @@ func BuildIdentifier(cfg *types.SandboxConfig, ownerID, chatID, assistantID stri
 // Returns the Computer, the resolved identifier, and any error.
 func GetComputer(ctx *agentContext.Context, cfg *types.SandboxConfig, manager *infra.Manager, conn ...connector.Connector) (infra.Computer, string, error) {
 	ownerID := resolveOwnerID(ctx)
-	identifier := BuildIdentifier(cfg, ownerID, ctx.ChatID, ctx.AssistantID, ctx.Metadata)
-
-	// Fill runtime fields.
-	cfg.Owner = ownerID
-	cfg.ID = identifier
 
 	workspaceID := ""
 	if ctx.Metadata != nil {
@@ -59,6 +54,12 @@ func GetComputer(ctx *agentContext.Context, cfg *types.SandboxConfig, manager *i
 	if workspaceID == "" {
 		workspaceID = ownerID
 	}
+
+	identifier := BuildIdentifier(cfg, ownerID, ctx.ChatID, ctx.AssistantID, workspaceID, ctx.Metadata)
+
+	// Fill runtime fields.
+	cfg.Owner = ownerID
+	cfg.ID = identifier
 	cfg.WorkspaceID = workspaceID
 
 	// Resolve computer_id from metadata to determine kind and nodeID.
diff --git a/agent/sandbox/v2/lifecycle_test.go b/agent/sandbox/v2/lifecycle_test.go
index 64cf2a81..4d1afe4d 100644
--- a/agent/sandbox/v2/lifecycle_test.go
+++ b/agent/sandbox/v2/lifecycle_test.go
@@ -20,7 +20,7 @@ import (
 
 func TestBuildIdentifier_Oneshot(t *testing.T) {
 	cfg := &types.SandboxConfig{Lifecycle: "oneshot"}
-	id := sandboxv2.BuildIdentifier(cfg, "owner1", "chat1", "ast1", nil)
+	id := sandboxv2.BuildIdentifier(cfg, "owner1", "chat1", "ast1", "ws1", nil)
 	if id != "" {
 		t.Errorf("oneshot should return empty, got %q", id)
 	}
@@ -28,7 +28,7 @@ func TestBuildIdentifier_Oneshot(t *testing.T) {
 
 func TestBuildIdentifier_Session(t *testing.T) {
 	cfg := &types.SandboxConfig{Lifecycle: "session"}
-	id := sandboxv2.BuildIdentifier(cfg, "owner1", "chat42", "ast1", nil)
+	id := sandboxv2.BuildIdentifier(cfg, "owner1", "chat42", "ast1", "ws1", nil)
 	if id != "owner1-chat42" {
 		t.Errorf("session: got %q, want %q", id, "owner1-chat42")
 	}
@@ -36,33 +36,33 @@ func TestBuildIdentifier_Session(t *testing.T) {
 
 func TestBuildIdentifier_Longrunning(t *testing.T) {
 	cfg := &types.SandboxConfig{Lifecycle: "longrunning"}
-	id := sandboxv2.BuildIdentifier(cfg, "owner1", "chat1", "ast99", nil)
-	if id != "owner1-ast99" {
-		t.Errorf("longrunning: got %q, want %q", id, "owner1-ast99")
+	id := sandboxv2.BuildIdentifier(cfg, "owner1", "chat1", "ast99", "ws1", nil)
+	if id != "owner1-ast99.ws1" {
+		t.Errorf("longrunning: got %q, want %q", id, "owner1-ast99.ws1")
 	}
 }
 
 func TestBuildIdentifier_Persistent(t *testing.T) {
 	cfg := &types.SandboxConfig{Lifecycle: "persistent"}
-	id := sandboxv2.BuildIdentifier(cfg, "owner1", "chat1", "ast99", nil)
-	if id != "owner1-ast99" {
-		t.Errorf("persistent: got %q, want %q", id, "owner1-ast99")
+	id := sandboxv2.BuildIdentifier(cfg, "owner1", "chat1", "ast99", "ws1", nil)
+	if id != "owner1-ast99.ws1" {
+		t.Errorf("persistent: got %q, want %q", id, "owner1-ast99.ws1")
 	}
 }
 
 func TestBuildIdentifier_MetadataOverride(t *testing.T) {
 	cfg := &types.SandboxConfig{Lifecycle: "session"}
 	meta := map[string]any{"computer_id": "custom-box"}
-	id := sandboxv2.BuildIdentifier(cfg, "owner1", "chat1", "ast1", meta)
-	if id != "owner1-custom-box" {
-		t.Errorf("metadata override: got %q, want %q", id, "owner1-custom-box")
+	id := sandboxv2.BuildIdentifier(cfg, "owner1", "chat1", "ast1", "ws1", meta)
+	if id != "owner1-custom-box.ws1" {
+		t.Errorf("metadata override: got %q, want %q", id, "owner1-custom-box.ws1")
 	}
 }
 
 func TestBuildIdentifier_MetadataEmptyIgnored(t *testing.T) {
 	cfg := &types.SandboxConfig{Lifecycle: "session"}
 	meta := map[string]any{"computer_id": ""}
-	id := sandboxv2.BuildIdentifier(cfg, "owner1", "chat42", "ast1", meta)
+	id := sandboxv2.BuildIdentifier(cfg, "owner1", "chat42", "ast1", "ws1", meta)
 	if id != "owner1-chat42" {
 		t.Errorf("empty metadata should fall through to session, got %q", id)
 	}
@@ -70,7 +70,7 @@ func TestBuildIdentifier_MetadataEmptyIgnored(t *testing.T) {
 
 func TestBuildIdentifier_UnknownLifecycle(t *testing.T) {
 	cfg := &types.SandboxConfig{Lifecycle: "unknown"}
-	id := sandboxv2.BuildIdentifier(cfg, "owner1", "chat1", "ast1", nil)
+	id := sandboxv2.BuildIdentifier(cfg, "owner1", "chat1", "ast1", "ws1", nil)
 	if id != "" {
 		t.Errorf("unknown lifecycle should return empty, got %q", id)
 	}
diff --git a/agent/sandbox/v2/options.go b/agent/sandbox/v2/options.go
index 2ceb3392..2ac6ce92 100644
--- a/agent/sandbox/v2/options.go
+++ b/agent/sandbox/v2/options.go
@@ -34,6 +34,7 @@ func BuildCreateOptions(cfg *types.SandboxConfig, identifier, ownerID, workspace
 		MountMode:   cfg.Computer.MountMode,
 		WorkspaceID: workspaceID,
 		Labels:      cfg.Labels,
+		DisplayName: cfg.DisplayName,
 	}
 
 	if opts.Labels == nil {
diff --git a/agent/sandbox/v2/types/config.go b/agent/sandbox/v2/types/config.go
index 9eab224e..d5ec1196 100644
--- a/agent/sandbox/v2/types/config.go
+++ b/agent/sandbox/v2/types/config.go
@@ -32,6 +32,7 @@ type SandboxConfig struct {
 	NodeID      string            `json:"-" yaml:"-"`
 	Kind        string            `json:"-" yaml:"-"`
 	WorkspaceID string            `json:"-" yaml:"-"`
+	DisplayName string            `json:"-" yaml:"-"`
 }
 
 // ComputerFilter defines the query parameters for GET /computer/options.
diff --git a/openapi/computer/computer.go b/openapi/computer/computer.go
index e0c80837..93016184 100644
--- a/openapi/computer/computer.go
+++ b/openapi/computer/computer.go
@@ -45,7 +45,6 @@ type computerOption struct {
 	Image       string             `json:"image,omitempty"`
 	Policy      string             `json:"policy,omitempty"`
 	VNC         bool               `json:"vnc"`
-	Labels      map[string]string  `json:"labels,omitempty"`
 	System      computerSystemInfo `json:"system"`
 }
 
@@ -255,7 +254,10 @@ func boxToOption(b *sandboxv2.Box) computerOption {
 	snap := b.Snapshot()
 	info := b.ComputerInfo()
 
-	displayName := info.System.Hostname
+	displayName := info.DisplayName
+	if displayName == "" {
+		displayName = info.System.Hostname
+	}
 	if displayName == "" {
 		displayName = snap.ID
 	}
@@ -285,7 +287,6 @@ func boxToOption(b *sandboxv2.Box) computerOption {
 		Image:       snap.Image,
 		Policy:      string(snap.Policy),
 		VNC:         snap.VNC,
-		Labels:      snap.Labels,
 		System: computerSystemInfo{
 			OS:       info.System.OS,
 			Arch:     info.System.Arch,
diff --git a/openapi/sandbox/manage.go b/openapi/sandbox/manage.go
index 270c3d62..316d1c58 100644
--- a/openapi/sandbox/manage.go
+++ b/openapi/sandbox/manage.go
@@ -94,7 +94,6 @@ type sandboxResponse struct {
 	Owner        string            `json:"owner"`
 	Status       string            `json:"status"`
 	Policy       string            `json:"policy,omitempty"`
-	Labels       map[string]string `json:"labels,omitempty"`
 	Image        string            `json:"image,omitempty"`
 	Mode         string            `json:"mode,omitempty"`
 	Addr         string            `json:"addr,omitempty"`
@@ -110,7 +109,10 @@ func boxToResponse(b *sandboxv2.Box) sandboxResponse {
 	snap := b.Snapshot()
 	info := b.ComputerInfo()
 
-	displayName := info.System.Hostname
+	displayName := info.DisplayName
+	if displayName == "" {
+		displayName = info.System.Hostname
+	}
 	if displayName == "" {
 		displayName = snap.ID
 	}
@@ -137,7 +139,6 @@ func boxToResponse(b *sandboxv2.Box) sandboxResponse {
 		Owner:        snap.Owner,
 		Status:       snap.Status,
 		Policy:       string(snap.Policy),
-		Labels:       snap.Labels,
 		Image:        snap.Image,
 		Mode:         mode,
 		Addr:         addr,
diff --git a/sandbox/v2/box.go b/sandbox/v2/box.go
index aed45d11..d8412014 100644
--- a/sandbox/v2/box.go
+++ b/sandbox/v2/box.go
@@ -30,6 +30,7 @@ type Box struct {
 	image         string
 	workspaceID   string
 	system        SystemInfo
+	displayName   string
 	workDir       string
 	ws            taiworkspace.FS
 	manager       *Manager
@@ -56,6 +57,7 @@ func (b *Box) ComputerInfo() ComputerInfo {
 		Image:       b.image,
 		Policy:      b.policy,
 		Labels:      b.labels,
+		DisplayName: b.displayName,
 	}
 }
 
diff --git a/sandbox/v2/manager.go b/sandbox/v2/manager.go
index 3306d95d..4f0fe5aa 100644
--- a/sandbox/v2/manager.go
+++ b/sandbox/v2/manager.go
@@ -3,7 +3,10 @@ package sandbox
 import (
 	"context"
 	"fmt"
+	"log"
 	"path/filepath"
+	goruntime "runtime"
+	"strconv"
 	"sync"
 	"time"
 
@@ -172,7 +175,9 @@ func (m *Manager) Create(ctx context.Context, opts CreateOptions) (*Box, error)
 		return nil, fmt.Errorf("sandbox: node %q has no container runtime", nodeID)
 	}
 
-	taiOpts := m.buildTaiCreateOptions(opts, nodeID, id)
+	sys := inferSystemInfo(ctx, res, opts.Image)
+
+	taiOpts := m.buildTaiCreateOptions(opts, nodeID, id, sys)
 
 	containerID, err := res.Runtime.Create(ctx, taiOpts)
 	if err != nil {
@@ -189,16 +194,6 @@ func (m *Manager) Create(ctx context.Context, opts CreateOptions) (*Box, error)
 		policy = Session
 	}
 
-	sys := SystemInfo{
-		OS:       res.System.OS,
-		Arch:     res.System.Arch,
-		Hostname: res.System.Hostname,
-		NumCPU:   res.System.NumCPU,
-		TotalMem: res.System.TotalMem,
-		Shell:    res.System.Shell,
-		TempDir:  res.System.TempDir,
-	}
-
 	boxWorkDir := opts.WorkDir
 	if boxWorkDir == "" {
 		boxWorkDir = "/workspace"
@@ -220,6 +215,7 @@ func (m *Manager) Create(ctx context.Context, opts CreateOptions) (*Box, error)
 		image:        opts.Image,
 		workspaceID:  opts.WorkspaceID,
 		workDir:      boxWorkDir,
+		displayName:  opts.DisplayName,
 		system:       sys,
 	}
 	box.lastCall.Store(time.Now().UnixMilli())
@@ -348,7 +344,7 @@ func (m *Manager) getNode(name string) (*tai.ConnResources, error) {
 	return res, nil
 }
 
-func (m *Manager) buildTaiCreateOptions(opts CreateOptions, nodeID, sandboxID string) tairuntime.CreateOptions {
+func (m *Manager) buildTaiCreateOptions(opts CreateOptions, nodeID, sandboxID string, sys SystemInfo) tairuntime.CreateOptions {
 	env := make(map[string]string)
 
 	reg := registry.Global()
@@ -378,6 +374,27 @@ func (m *Manager) buildTaiCreateOptions(opts CreateOptions, nodeID, sandboxID st
 	if opts.WorkspaceID != "" {
 		labels["workspace-id"] = opts.WorkspaceID
 	}
+	if opts.DisplayName != "" {
+		labels["sandbox-display-name"] = opts.DisplayName
+	}
+	if sys.OS != "" {
+		labels["sandbox-sys-os"] = sys.OS
+	}
+	if sys.Arch != "" {
+		labels["sandbox-sys-arch"] = sys.Arch
+	}
+	if sys.Hostname != "" {
+		labels["sandbox-sys-hostname"] = sys.Hostname
+	}
+	if sys.NumCPU > 0 {
+		labels["sandbox-sys-numcpu"] = strconv.Itoa(sys.NumCPU)
+	}
+	if sys.TotalMem > 0 {
+		labels["sandbox-sys-totalmem"] = strconv.FormatInt(sys.TotalMem, 10)
+	}
+	if sys.Shell != "" {
+		labels["sandbox-sys-shell"] = sys.Shell
+	}
 	for k, v := range opts.Labels {
 		labels[k] = v
 	}
@@ -467,6 +484,10 @@ func (m *Manager) recoverBoxes(ctx context.Context, nodeID string, res *tai.Conn
 				}
 			}
 		}
+		sys := systemInfoFromLabels(c.Labels)
+		if sys.OS == "" {
+			sys = inferSystemInfo(ctx, res, c.Image)
+		}
 		box := &Box{
 			id:          sandboxID,
 			containerID: cid,
@@ -479,6 +500,8 @@ func (m *Manager) recoverBoxes(ctx context.Context, nodeID string, res *tai.Conn
 			workspaceID: c.Labels["workspace-id"],
 			vnc:         hasVNC,
 			workDir:     "/workspace",
+			displayName: c.Labels["sandbox-display-name"],
+			system:      sys,
 			manager:     m,
 		}
 		box.lastCall.Store(time.Now().UnixMilli())
@@ -486,6 +509,51 @@ func (m *Manager) recoverBoxes(ctx context.Context, nodeID string, res *tai.Conn
 	}
 }
 
+// inferSystemInfo derives static SystemInfo for a container from image metadata
+// and Tai host resources. OS/Arch/Shell come from the image; Hostname/NumCPU/TotalMem
+// come from the Tai host.
+func inferSystemInfo(ctx context.Context, res *tai.ConnResources, imageRef string) SystemInfo {
+	sys := SystemInfo{
+		Hostname: res.System.Hostname,
+		NumCPU:   res.System.NumCPU,
+		TotalMem: res.System.TotalMem,
+	}
+
+	if res.Image != nil {
+		meta, err := res.Image.Inspect(ctx, imageRef)
+		if err != nil {
+			log.Printf("[sandbox/v2] image inspect %q: %v (using fallback)", imageRef, err)
+		}
+		if meta != nil {
+			sys.OS = meta.OS
+			sys.Arch = meta.Arch
+			sys.Shell = meta.Shell
+			return sys
+		}
+	}
+
+	sys.OS = "linux"
+	sys.Arch = goruntime.GOARCH
+	sys.Shell = "bash"
+	return sys
+}
+
+// systemInfoFromLabels restores SystemInfo from Docker container labels that
+// were persisted at creation time, so recovery doesn't depend on the Tai node
+// being connected.
+func systemInfoFromLabels(labels map[string]string) SystemInfo {
+	numCPU, _ := strconv.Atoi(labels["sandbox-sys-numcpu"])
+	totalMem, _ := strconv.ParseInt(labels["sandbox-sys-totalmem"], 10, 64)
+	return SystemInfo{
+		OS:       labels["sandbox-sys-os"],
+		Arch:     labels["sandbox-sys-arch"],
+		Hostname: labels["sandbox-sys-hostname"],
+		NumCPU:   numCPU,
+		TotalMem: totalMem,
+		Shell:    labels["sandbox-sys-shell"],
+	}
+}
+
 // ImageExists reports whether the given image ref exists on the target node.
 func (m *Manager) ImageExists(ctx context.Context, nodeID, ref string) (bool, error) {
 	res, err := m.getNode(nodeID)
diff --git a/sandbox/v2/types.go b/sandbox/v2/types.go
index bc78c85a..828ef799 100644
--- a/sandbox/v2/types.go
+++ b/sandbox/v2/types.go
@@ -44,6 +44,7 @@ type ComputerInfo struct {
 	Image       string
 	Policy      LifecyclePolicy
 	Labels      map[string]string
+	DisplayName string
 }
 
 // SystemInfo describes the hardware and environment of a Tai node.
@@ -104,6 +105,7 @@ type CreateOptions struct {
 	WorkspaceID string
 	MountMode   string
 	MountPath   string
+	DisplayName string
 }
 
 type ListOptions struct {
diff --git a/tai/runtime/image.go b/tai/runtime/image.go
index 45e32209..e18b0e27 100644
--- a/tai/runtime/image.go
+++ b/tai/runtime/image.go
@@ -8,11 +8,20 @@ import (
 // Image manages container images on a runtime node.
 type Image interface {
 	Exists(ctx context.Context, ref string) (bool, error)
+	Inspect(ctx context.Context, ref string) (*ImageMeta, error)
 	Pull(ctx context.Context, ref string, opts PullOptions) (<-chan PullProgress, error)
 	Remove(ctx context.Context, ref string, force bool) error
 	List(ctx context.Context) ([]ImageInfo, error)
 }
 
+// ImageMeta holds static metadata extracted from a container image.
+type ImageMeta struct {
+	OS      string // "linux", "windows"
+	Arch    string // "amd64", "arm64"
+	Shell   string // preferred shell: "bash", "sh", "cmd.exe", "pwsh"
+	WorkDir string // default working directory from Dockerfile WORKDIR
+}
+
 // PullOptions configures an image pull operation.
 type PullOptions struct {
 	Auth *RegistryAuth // nil = anonymous / public
diff --git a/tai/runtime/image_docker.go b/tai/runtime/image_docker.go
index 09b3edb9..4014bde1 100644
--- a/tai/runtime/image_docker.go
+++ b/tai/runtime/image_docker.go
@@ -6,6 +6,7 @@ import (
 	"encoding/json"
 	"fmt"
 	"io"
+	"strings"
 	"time"
 
 	"github.com/docker/docker/api/types/image"
@@ -35,6 +36,44 @@ func (d *dockerImage) Exists(ctx context.Context, ref string) (bool, error) {
 	return true, nil
 }
 
+func (d *dockerImage) Inspect(ctx context.Context, ref string) (*ImageMeta, error) {
+	inspect, _, err := d.cli.ImageInspectWithRaw(ctx, ref)
+	if err != nil {
+		return nil, fmt.Errorf("image inspect %q: %w", ref, err)
+	}
+
+	meta := &ImageMeta{
+		OS:   inspect.Os,
+		Arch: inspect.Architecture,
+	}
+
+	if inspect.Config != nil {
+		meta.WorkDir = inspect.Config.WorkingDir
+
+		if len(inspect.Config.Shell) > 0 {
+			meta.Shell = inspect.Config.Shell[0]
+		}
+		if meta.Shell == "" {
+			for _, e := range inspect.Config.Env {
+				if strings.HasPrefix(e, "SHELL=") {
+					meta.Shell = e[6:]
+					break
+				}
+			}
+		}
+	}
+
+	if meta.Shell == "" {
+		if strings.EqualFold(meta.OS, "windows") {
+			meta.Shell = "cmd.exe"
+		} else {
+			meta.Shell = "bash"
+		}
+	}
+
+	return meta, nil
+}
+
 func (d *dockerImage) Pull(ctx context.Context, ref string, opts PullOptions) (<-chan PullProgress, error) {
 	pullOpts := image.PullOptions{}
 	if opts.Auth != nil {
diff --git a/tai/runtime/image_k8s.go b/tai/runtime/image_k8s.go
index bd81a425..2a22952b 100644
--- a/tai/runtime/image_k8s.go
+++ b/tai/runtime/image_k8s.go
@@ -12,6 +12,10 @@ func (k *k8sImage) Exists(_ context.Context, _ string) (bool, error) {
 	return true, nil
 }
 
+func (k *k8sImage) Inspect(_ context.Context, _ string) (*ImageMeta, error) {
+	return nil, nil
+}
+
 func (k *k8sImage) Pull(_ context.Context, _ string, _ PullOptions) (<-chan PullProgress, error) {
 	return nil, nil
 }
diff --git a/tai/tunnel/forward.go b/tai/tunnel/forward.go
index 1713de90..81ee5896 100644
--- a/tai/tunnel/forward.go
+++ b/tai/tunnel/forward.go
@@ -113,17 +113,26 @@ func resolveTargetPort(c *gin.Context, node *types.NodeMeta) int {
 	return 0
 }
 
-// rewriteRequest clones the request and strips everything up to and including
-// /tai/:taiID from the path, handling any baseURL prefix (e.g. /v1/tai/abc/proxy/x → /proxy/x).
+// rewriteRequest clones the request and strips the Yao-side route prefix,
+// leaving only what the Tai-side handler expects.
+//
+// The Tai httpproxy expects /{containerID}:{port}/..., so the /proxy prefix
+// is stripped. The Tai VNC router expects /vnc/{containerID}/ws, so the /vnc
+// prefix is kept.
+//
+//	/v1/tai/abc/proxy/cid:8080/foo → /cid:8080/foo
+//	/v1/tai/abc/vnc/cid/ws        → /vnc/cid/ws
 func rewriteRequest(orig *http.Request, taiID string) *http.Request {
 	r := orig.Clone(orig.Context())
 
 	marker := "/tai/" + taiID
 	if idx := strings.Index(r.URL.Path, marker); idx >= 0 {
-		r.URL.Path = r.URL.Path[idx+len(marker):]
-		if r.URL.Path == "" {
-			r.URL.Path = "/"
+		rest := r.URL.Path[idx+len(marker):]
+		rest = strings.TrimPrefix(rest, "/proxy")
+		if rest == "" {
+			rest = "/"
 		}
+		r.URL.Path = rest
 	}
 
 	r.RequestURI = r.URL.RequestURI()
diff --git a/tai/tunnel/forward_test.go b/tai/tunnel/forward_test.go
index 3259cc67..703e5198 100644
--- a/tai/tunnel/forward_test.go
+++ b/tai/tunnel/forward_test.go
@@ -84,8 +84,8 @@ func TestRewriteRequest(t *testing.T) {
 			"proxy_path",
 			"/tai/abc123/proxy/api/v1/data",
 			"abc123",
-			"/proxy/api/v1/data",
-			"/proxy/api/v1/data",
+			"/api/v1/data",
+			"/api/v1/data",
 		},
 		{
 			"vnc_path",
@@ -98,8 +98,8 @@ func TestRewriteRequest(t *testing.T) {
 			"with_query",
 			"/tai/node-1/proxy/api?foo=bar",
 			"node-1",
-			"/proxy/api",
-			"/proxy/api?foo=bar",
+			"/api",
+			"/api?foo=bar",
 		},
 		{
 			"exact_prefix",
@@ -112,8 +112,8 @@ func TestRewriteRequest(t *testing.T) {
 			"with_base_url",
 			"/v1/tai/node-1/proxy/api/v1/data",
 			"node-1",
-			"/proxy/api/v1/data",
-			"/proxy/api/v1/data",
+			"/api/v1/data",
+			"/api/v1/data",
 		},
 		{
 			"with_base_url_vnc",
@@ -122,6 +122,13 @@ func TestRewriteRequest(t *testing.T) {
 			"/vnc/__host__/ws",
 			"/vnc/__host__/ws",
 		},
+		{
+			"proxy_container_port",
+			"/v1/tai/abc/proxy/cid123:8080/foo",
+			"abc",
+			"/cid123:8080/foo",
+			"/cid123:8080/foo",
+		},
 		{
 			"no_match",
 			"/other/path",