diff --git a/internal/dockerlab/dockerlab_test.go b/internal/dockerlab/dockerlab_test.go
index 0bb0042..2efa9bb 100644
--- a/internal/dockerlab/dockerlab_test.go
+++ b/internal/dockerlab/dockerlab_test.go
@@ -71,6 +71,21 @@ type fakeDockerRunner struct {
 	networkOrder      []string
 	networkCreates    int
 	failNetworkCreate bool
+	// contextFailure makes every invocation fail the way the Docker CLI does
+	// when the selected context cannot be resolved.
+	contextFailure bool
+	// contextFailureOnNetworkRemove fails only network removal that way.
+	contextFailureOnNetworkRemove bool
+}
+
+// contextNotFoundMessage is the Docker CLI's output when the selected
+// context is missing, captured from Docker 29.7.2.
+const contextNotFoundMessage = `Failed to initialize: unable to resolve docker endpoint: context "opsquest-missing-context": context not found: open /home/player/.docker/contexts/meta/fdff/meta.json: no such file or directory`
+
+func (r *fakeDockerRunner) setContextFailure(failing bool) {
+	r.mutex.Lock()
+	defer r.mutex.Unlock()
+	r.contextFailure = failing
 }
 
 func newFakeDockerRunner() *fakeDockerRunner {
@@ -92,6 +107,9 @@ func (r *fakeDockerRunner) run(ctx context.Context, args ...string) (runResult,
 		return runResult{}, err
 	}
 	r.calls = append(r.calls, append([]string(nil), args...))
+	if r.contextFailure {
+		return runResult{stderr: contextNotFoundMessage}, errors.New("exit status 1")
+	}
 
 	switch {
 	case hasPrefix(args, "context", "show"):
@@ -345,6 +363,8 @@ func (r *fakeDockerRunner) run(ctx context.Context, args ...string) (runResult,
 			}
 		}
 		return runResult{stdout: output.String()}, nil
+	case hasPrefix(args, "network", "rm") && r.contextFailureOnNetworkRemove:
+		return runResult{stderr: contextNotFoundMessage}, errors.New("exit status 1")
 	case hasPrefix(args, "network", "rm"):
 		id := args[len(args)-1]
 		network, exists := r.networks[id]
diff --git a/internal/dockerlab/janitor.go b/internal/dockerlab/janitor.go
index 7610c31..e16818c 100644
--- a/internal/dockerlab/janitor.go
+++ b/internal/dockerlab/janitor.go
@@ -67,7 +67,7 @@ func (f *Factory) removeOrphans(ctx context.Context) (int, error) {
 	}
 	for _, id := range orphans.networks {
 		result, err := runDocker(ctx, f.runner, "network", "rm", id)
-		if err != nil && !isMissingNetwork(result) {
+		if err != nil && !isMissingNetwork(result, id) {
 			removeErrors = append(removeErrors, fmt.Errorf("remove orphaned Docker network %s: %w", id[:12], err))
 			continue
 		}
diff --git a/internal/dockerlab/network.go b/internal/dockerlab/network.go
index 6920b7c..9e9cd6b 100644
--- a/internal/dockerlab/network.go
+++ b/internal/dockerlab/network.go
@@ -145,7 +145,7 @@ func (e *environment) inspectNetworkUnchecked(ctx context.Context, network *trac
 func inspectNetworkReference(ctx context.Context, commandRunner runner, reference string) (networkInspection, bool, error) {
 	result, err := runDocker(ctx, commandRunner, "network", "inspect", "--format", "{{json .}}", reference)
 	if err != nil {
-		if isMissingNetwork(result) {
+		if isMissingNetwork(result, reference) {
 			return networkInspection{}, false, nil
 		}
 		return networkInspection{}, false, err
@@ -157,9 +157,19 @@ func inspectNetworkReference(ctx context.Context, commandRunner runner, referenc
 	return inspection, true, nil
 }
 
-func isMissingNetwork(result runResult) bool {
+// isMissingNetwork reports whether Docker said that exactly reference does
+// not exist. It accepts only the engine's network-specific wording that names
+// the reference, so CLI, context, and transport failures such as
+// `context "x": context not found` propagate as errors instead of looking
+// like a removed network.
+func isMissingNetwork(result runResult, reference string) bool {
+	if reference == "" {
+		return false
+	}
 	message := strings.ToLower(result.stderr + "\n" + result.stdout)
-	return strings.Contains(message, "no such network") || strings.Contains(message, "not found")
+	reference = strings.ToLower(reference)
+	return strings.Contains(message, "network "+reference+" not found") ||
+		strings.Contains(message, "no such network: "+reference)
 }
 
 // attachedTo reports whether a container inspection shows an endpoint on
@@ -477,7 +487,7 @@ func (e *environment) closeNetworks(ctx context.Context, networks []*trackedNetw
 			continue
 		}
 		network.id = inspection.ID
-		if result, err := e.run(ctx, "network", "rm", inspection.ID); err != nil && !isMissingNetwork(result) {
+		if result, err := e.run(ctx, "network", "rm", inspection.ID); err != nil && !isMissingNetwork(result, inspection.ID) {
 			cleanupErrors = append(cleanupErrors, fmt.Errorf("remove Docker network %s: %w", network.name, err))
 			unresolved = append(unresolved, network)
 		}
diff --git a/internal/dockerlab/network_test.go b/internal/dockerlab/network_test.go
index 2cc72bb..b00d371 100644
--- a/internal/dockerlab/network_test.go
+++ b/internal/dockerlab/network_test.go
@@ -391,3 +391,86 @@ func TestNetworkErrorsRedactExactIdentity(t *testing.T) {
 		t.Fatalf("redactNetworkIdentifiers() = %q", got)
 	}
 }
+
+func TestMissingNetworkClassificationIsReferenceSpecific(t *testing.T) {
+	name := "opsquest-" + strings.Repeat("a", 24) + "-n01"
+	id := "feed" + strings.Repeat("0", 59) + "1"
+	tests := []struct {
+		name      string
+		stderr    string
+		reference string
+		want      bool
+	}{
+		{name: "daemon missing name", stderr: "Error response from daemon: network " + name + " not found", reference: name, want: true},
+		{name: "daemon missing ID", stderr: "Error response from daemon: network " + id + " not found", reference: id, want: true},
+		{name: "legacy CLI wording", stderr: "Error: No such network: " + name, reference: name, want: true},
+		{name: "context not found", stderr: contextNotFoundMessage, reference: name},
+		{name: "different network", stderr: "Error response from daemon: network other-net not found", reference: name},
+		{name: "daemon unreachable", stderr: "Cannot connect to the Docker daemon at unix:///var/run/docker.sock. Is the docker daemon running?", reference: name},
+		{name: "empty reference", stderr: "Error response from daemon: network  not found", reference: ""},
+	}
+	for _, test := range tests {
+		if got := isMissingNetwork(runResult{stderr: test.stderr}, test.reference); got != test.want {
+			t.Errorf("%s: isMissingNetwork() = %v, want %v", test.name, got, test.want)
+		}
+	}
+}
+
+func TestContextFailureNeitherPassesValidationNorDropsNetworkCleanup(t *testing.T) {
+	commandRunner := newFakeDockerRunner()
+	environment := createEnvironmentForMission(t, commandRunner, testNetworkDockerMission())
+	networks := commandRunner.networkCount()
+	if networks != 3 {
+		t.Fatalf("fixture networks = %d, want 3", networks)
+	}
+
+	commandRunner.setContextFailure(true)
+	absent := mission.Condition{Type: mission.ConditionDockerNetworkAbsent, Network: "db-net"}
+	if got, err := environment.Observe(context.Background(), absent); err == nil || got || !strings.Contains(err.Error(), "context not found") {
+		t.Fatalf("Observe(network absent) during context failure = %v, %v; want error", got, err)
+	}
+	shared := networkCondition(mission.ConditionDockerNetworkShared, "web", "api")
+	if got, err := environment.Observe(context.Background(), shared); err == nil || got {
+		t.Fatalf("Observe(shared) during context failure = %v, %v; want error", got, err)
+	}
+	if err := environment.Close(); err == nil {
+		t.Fatal("Close() during context failure reported success")
+	}
+	if commandRunner.networkCount() != networks {
+		t.Fatalf("networks changed during failed Close: %d", commandRunner.networkCount())
+	}
+
+	commandRunner.setContextFailure(false)
+	if err := environment.Close(); err != nil {
+		t.Fatalf("Close() after context recovery = %v", err)
+	}
+	if commandRunner.networkCount() != 0 || commandRunner.containerCount() != 0 {
+		t.Fatalf("resources leaked after recovered Close: %d networks, %d containers", commandRunner.networkCount(), commandRunner.containerCount())
+	}
+}
+
+func TestJanitorPropagatesNetworkRemovalFailures(t *testing.T) {
+	commandRunner := newFakeDockerRunner()
+	session := strings.Repeat("1", 24)
+	orphan := "feed" + strings.Repeat("1", 60)
+	commandRunner.seedNetwork(orphan, &fakeNetwork{labels: orphanLabels(session, "999", testOwnerHost), name: "opsquest-" + session + "-n01", created: testNow})
+	factory := testFactory(commandRunner)
+
+	commandRunner.mutex.Lock()
+	commandRunner.contextFailureOnNetworkRemove = true
+	commandRunner.mutex.Unlock()
+	removed, err := factory.RemoveOrphanedResources(context.Background())
+	if err == nil || !strings.Contains(err.Error(), "context not found") || removed != 0 {
+		t.Fatalf("RemoveOrphanedResources() during context failure = %d, %v; want error and nothing counted", removed, err)
+	}
+	if !commandRunner.hasNetwork(orphan) {
+		t.Fatal("orphaned network disappeared during a failed removal")
+	}
+
+	commandRunner.mutex.Lock()
+	commandRunner.contextFailureOnNetworkRemove = false
+	commandRunner.mutex.Unlock()
+	if removed, err := factory.RemoveOrphanedResources(context.Background()); err != nil || removed != 1 || commandRunner.hasNetwork(orphan) {
+		t.Fatalf("RemoveOrphanedResources() after recovery = %d, %v", removed, err)
+	}
+}