diff --git a/internal/cli/stop.go b/internal/cli/stop.go
index 5c441e6..d514d49 100644
--- a/internal/cli/stop.go
+++ b/internal/cli/stop.go
@@ -77,7 +77,11 @@ func addStopFlags(cmd *cobra.Command, opts *stopOpts) {
 
 func runStopOrDown(ctx context.Context, out Output, opts stopOpts, remove bool) error {
 	if opts.workspaceFolder == "" {
-		opts.workspaceFolder, _ = os.Getwd()
+		wd, err := os.Getwd()
+		if err != nil {
+			return writeErrorResult(out, fmt.Sprintf("current directory: %v", err))
+		}
+		opts.workspaceFolder = wd
 	}
 
 	logger := log.New(log.Options{Writer: out.Stderr(), Format: "text"})
@@ -87,13 +91,20 @@ func runStopOrDown(ctx context.Context, out Output, opts stopOpts, remove bool)
 	}
 	defer engine.Close()
 
-	id := resolveWorkspaceContainer(ctx, engine, opts)
+	id, err := resolveWorkspaceContainer(ctx, engine, opts)
+	if err != nil {
+		return writeErrorResult(out, err.Error())
+	}
 	if id == "" {
 		return writeSuccessJSON(out, map[string]any{"outcome": "success", "result": "no-container-found"})
 	}
 
+	insp, err := engine.InspectContainer(ctx, id)
+	if err != nil {
+		return writeErrorResult(out, fmt.Sprintf("inspect container %s: %v", id, err))
+	}
 	project := ""
-	if insp, ierr := engine.InspectContainer(ctx, id); ierr == nil && insp.Config != nil {
+	if insp.Config != nil {
 		project = insp.Config.Labels["com.docker.compose.project"]
 	}
 
@@ -129,14 +140,13 @@ func runStopOrDown(ctx context.Context, out Output, opts stopOpts, remove bool)
 	})
 }
 
-func resolveWorkspaceContainer(ctx context.Context, engine *docker.EngineClient, opts stopOpts) string {
+func resolveWorkspaceContainer(ctx context.Context, engine *docker.EngineClient, opts stopOpts) (string, error) {
 	if opts.containerID != "" {
-		return opts.containerID
+		return opts.containerID, nil
 	}
 	configFile := ""
 	if opts.configPath != "" {
 		configFile = resolvePath(opts.configPath)
 	}
-	id, _ := resolveContainerID(ctx, engine, opts.workspaceFolder, configFile, opts.idLabels)
-	return id
+	return resolveContainerID(ctx, engine, opts.workspaceFolder, configFile, opts.idLabels)
 }
diff --git a/internal/cli/stop_held_test.go b/internal/cli/stop_held_test.go
index 630aa23..4a09e8c 100644
--- a/internal/cli/stop_held_test.go
+++ b/internal/cli/stop_held_test.go
@@ -20,6 +20,7 @@ type fakeEngine struct {
 	mu         sync.Mutex
 	containers map[string]map[string]string
 	stopFails  bool
+	listFails  bool
 	calls      []string
 }
 
@@ -69,6 +70,11 @@ func (e *fakeEngine) serve(w http.ResponseWriter, r *http.Request) {
 		}
 		slices.Sort(want)
 		e.record("list " + strings.Join(want, ","))
+		if e.listFails {
+			w.WriteHeader(http.StatusInternalServerError)
+			fmt.Fprint(w, `{"message":"cannot list"}`)
+			return
+		}
 		items := []map[string]string{}
 		for id, labels := range e.containers {
 			if hasLabels(labels, want) {
@@ -219,6 +225,42 @@ func TestStopWithNoContainerSucceedsWithoutDoingAnything(t *testing.T) {
 	}
 }
 
+func TestStopOrDownReportsALookupTheEngineRefused(t *testing.T) {
+	engine := startFakeEngine(t, map[string]map[string]string{})
+	engine.listFails = true
+	cli, _ := fakeDockerCLI(t, false, 0)
+
+	got := runStopOrDownForTest(t, stopOpts{workspaceFolder: t.TempDir(), dockerPath: cli}, true)
+
+	assertResult(t, got, map[string]any{"outcome": "error"})
+	if msg, _ := got["message"].(string); !strings.HasPrefix(msg, "Command failed: docker ps ") {
+		t.Errorf("message = %q, want the failed container lookup", msg)
+	}
+	for _, c := range engine.recorded() {
+		if !strings.HasPrefix(c, "list ") {
+			t.Errorf("engine call %q after the lookup failed", c)
+		}
+	}
+}
+
+func TestStopOrDownReportsAContainerItCannotInspect(t *testing.T) {
+	engine := startFakeEngine(t, map[string]map[string]string{})
+	cli, composeCalls := fakeDockerCLI(t, false, 0)
+
+	got := runStopOrDownForTest(t, stopOpts{containerID: "gone", dockerPath: cli}, false)
+
+	assertResult(t, got, map[string]any{"outcome": "error"})
+	if msg, _ := got["message"].(string); !strings.HasPrefix(msg, "inspect container gone: ") {
+		t.Errorf("message = %q, want the inspect failure", msg)
+	}
+	if calls := engine.recorded(); len(calls) != 0 {
+		t.Errorf("engine calls = %v after the inspect failed", calls)
+	}
+	if calls := composeCalls(); calls != nil {
+		t.Errorf("docker CLI ran %v", calls)
+	}
+}
+
 func TestDownStopsAndRemovesTheContainer(t *testing.T) {
 	engine := startFakeEngine(t, map[string]map[string]string{"c1": {}})
 	cli, _ := fakeDockerCLI(t, false, 0)
diff --git a/internal/docker/argbuilders_test.go b/internal/docker/argbuilders_test.go
index b268239..b6786aa 100644
--- a/internal/docker/argbuilders_test.go
+++ b/internal/docker/argbuilders_test.go
@@ -23,6 +23,7 @@ type cannedResponse struct {
 	stdout []byte
 	stderr []byte
 	code   int
+	err    error
 }
 
 func (r *recordingRunner) Run(_ context.Context, stream io.Writer, name string, args ...string) ([]byte, []byte, int, error) {
@@ -34,7 +35,7 @@ func (r *recordingRunner) Run(_ context.Context, stream io.Writer, name string,
 			_, _ = stream.Write(resp.stdout)
 			_, _ = stream.Write(resp.stderr)
 		}
-		return resp.stdout, resp.stderr, resp.code, nil
+		return resp.stdout, resp.stderr, resp.code, resp.err
 	}
 	return nil, nil, 0, nil
 }
diff --git a/internal/docker/builder_detect_held_test.go b/internal/docker/builder_detect_held_test.go
index 1af47a7..f3b0da3 100644
--- a/internal/docker/builder_detect_held_test.go
+++ b/internal/docker/builder_detect_held_test.go
@@ -1,6 +1,7 @@
 package docker
 
 import (
+	"errors"
 	"testing"
 
 	"github.com/devcontainers/cli/internal/log"
@@ -22,3 +23,14 @@ func TestBuilderDetectionIgnoresAFailedBuildx(t *testing.T) {
 		t.Errorf("FindDockerDriverBuilder after a failed ls = %q, want empty", got)
 	}
 }
+
+func TestFindDockerDriverBuilderWhenTheContextCannotBeRead(t *testing.T) {
+	rr := &recordingRunner{responses: []cannedResponse{
+		{err: errors.New("exec docker: no such file")},
+		{stdout: []byte("NAME DRIVER\nremote* docker-container running\ndefault docker running\n")},
+	}}
+	c := &Client{DockerPath: "docker", Log: log.Null, Runner: rr}
+	if got := c.FindDockerDriverBuilder(t.Context()); got != "default" {
+		t.Errorf("FindDockerDriverBuilder with no current context = %q, want the first docker-driver builder", got)
+	}
+}
diff --git a/internal/docker/client.go b/internal/docker/client.go
index 10ddf56..7ace159 100644
--- a/internal/docker/client.go
+++ b/internal/docker/client.go
@@ -218,8 +218,10 @@ func (c *Client) DetectActiveBuilder(ctx context.Context) *BuilderInfo {
 }
 
 func (c *Client) FindDockerDriverBuilder(ctx context.Context) string {
-	ctxRes, _ := c.Run(ctx, "context", "inspect", "--format", "{{.Name}}")
-	currentContext := strings.TrimSpace(string(ctxRes.Stdout))
+	currentContext := ""
+	if ctxRes, err := c.Run(ctx, "context", "inspect", "--format", "{{.Name}}"); err == nil && ctxRes.ExitCode == 0 {
+		currentContext = strings.TrimSpace(string(ctxRes.Stdout))
+	}
 
 	res, err := c.Run(ctx, "buildx", "ls")
 	if err != nil || res.ExitCode != 0 {
diff --git a/internal/lifecycle/probe.go b/internal/lifecycle/probe.go
index 02d074a..1643bfb 100644
--- a/internal/lifecycle/probe.go
+++ b/internal/lifecycle/probe.go
@@ -171,7 +171,10 @@ func ProbedRemoteEnv(ctx context.Context, exec ContainerExecutor, logger log.Log
 	}
 	server := NewShellServer(ctx, exec, containerID, remoteUser)
 	defer server.Close()
-	env, _ := ProbeRemoteEnv(logger, server, strategy, remoteUser, sessionDataFolder)
+	env, err := ProbeRemoteEnv(logger, server, strategy, remoteUser, sessionDataFolder)
+	if err != nil {
+		logger.Write(log.ToErrorText(err.Error()), log.LevelInfo)
+	}
 	if env == nil {
 		env = map[string]string{}
 	}
diff --git a/internal/lifecycle/shell_test.go b/internal/lifecycle/shell_test.go
index 1cb09a4..19c36bd 100644
--- a/internal/lifecycle/shell_test.go
+++ b/internal/lifecycle/shell_test.go
@@ -1,8 +1,10 @@
 package lifecycle
 
 import (
+	"bytes"
 	"context"
 	"errors"
+	"strings"
 	"testing"
 
 	"github.com/devcontainers/cli/internal/log"
@@ -119,7 +121,12 @@ func TestProbedRemoteEnv(t *testing.T) {
 	}
 
 	fe = &fakeExecutor{fn: func(string) (string, string, int, error) { return "", "", 1, errors.New("no shell") }}
-	if env := ProbedRemoteEnv(t.Context(), fe, log.Null, "cid", "vscode", ProbeLoginShell, ""); env == nil || len(env) != 0 {
+	var logged bytes.Buffer
+	logger := log.New(log.Options{Level: log.LevelInfo, Format: "text", Writer: &logged})
+	if env := ProbedRemoteEnv(t.Context(), fe, logger, "cid", "vscode", ProbeLoginShell, ""); env == nil || len(env) != 0 {
 		t.Fatalf("failed probe: env = %v, want empty", env)
 	}
+	if !strings.Contains(logged.String(), "no shell") {
+		t.Errorf("failed probe logged %q, want the probe's error", logged.String())
+	}
 }
diff --git a/internal/log/log.go b/internal/log/log.go
index 65de9e1..a3e0b4e 100644
--- a/internal/log/log.go
+++ b/internal/log/log.go
@@ -284,6 +284,14 @@ const (
 	numberColor    = "38;2;86;156;214"
 )
 
+func ToErrorText(s string) string {
+	lines := newlines.Split(s, -1)
+	for i, l := range lines {
+		lines[i] = color("31", l)
+	}
+	return strings.Join(lines, "\r\n") + "\r\n"
+}
+
 func color(c, s string) string {
 	return "\x1b[1m\x1b[" + c + "m" + s + "\x1b[39m\x1b[22m"
 }
diff --git a/internal/log/log_test.go b/internal/log/log_test.go
index e3ac32d..8369367 100644
--- a/internal/log/log_test.go
+++ b/internal/log/log_test.go
@@ -189,3 +189,10 @@ func TestLogLevelFilter_TerminalVsJSON(t *testing.T) {
 		t.Errorf("json must emit all levels, got %q", js)
 	}
 }
+
+func TestToErrorTextMatchesTheReference(t *testing.T) {
+	want := "\x1b[1m\x1b[31mfirst\x1b[39m\x1b[22m\r\n\x1b[1m\x1b[31msecond\x1b[39m\x1b[22m\r\n"
+	if got := ToErrorText("first\r\nsecond"); got != want {
+		t.Errorf("ToErrorText = %q, want %q", got, want)
+	}
+}