diff --git a/packages/cli/src/context.ts b/packages/cli/src/context.ts
index 651376b5c..59aaad3ff 100644
--- a/packages/cli/src/context.ts
+++ b/packages/cli/src/context.ts
@@ -6,11 +6,15 @@
  */
 
 import { homedir } from "node:os";
+import { isAbsolute } from "node:path";
 import type { CommandContext } from "@stricli/core";
 import { getConfigDir } from "./lib/db/index.js";
+import { logger } from "./lib/logger.js";
 import { type Span, setCommandSpanName } from "./lib/telemetry.js";
 import type { Writer } from "./types/index.js";
 
+const log = logger.withTag("context");
+
 export interface SentryContext extends CommandContext {
   readonly process: NodeJS.Process;
   readonly env: NodeJS.ProcessEnv;
@@ -30,6 +34,28 @@ export interface SentryContext extends CommandContext {
   readonly commandPrefix?: readonly string[];
 }
 
+/**
+ * Resolve the working directory, tolerating one that has been deleted.
+ *
+ * `process.cwd()` throws ENOENT (`uv_cwd`) once the directory the CLI was
+ * started in is removed (e.g. an agent's git worktree cleaned up under it).
+ * The shell's logical `PWD` still names that directory, so use it instead:
+ * lookups under the missing path find nothing, and commands that don't need
+ * local files keep working.
+ */
+function resolveCwd(process: NodeJS.Process): string {
+  try {
+    return process.cwd();
+  } catch (error) {
+    const pwd = process.env.PWD;
+    if (!(pwd && isAbsolute(pwd))) {
+      throw error;
+    }
+    log.debug(`Working directory is unavailable, using PWD (${pwd})`, error);
+    return pwd;
+  }
+}
+
 /**
  * Build a dynamic context that uses forCommand to set telemetry tags.
  *
@@ -43,7 +69,7 @@ export function buildContext(process: NodeJS.Process, span?: Span) {
   const baseContext: SentryContext = {
     process,
     env: process.env,
-    cwd: process.cwd(),
+    cwd: resolveCwd(process),
     homeDir: homedir(),
     configDir: getConfigDir(),
     stdout: process.stdout,
diff --git a/packages/cli/test/lib/context.test.ts b/packages/cli/test/lib/context.test.ts
new file mode 100644
index 000000000..2baf37202
--- /dev/null
+++ b/packages/cli/test/lib/context.test.ts
@@ -0,0 +1,46 @@
+import { afterEach, describe, expect, test, vi } from "vitest";
+import { buildContext } from "../../src/context.js";
+
+/** Mirrors the error Node throws when the working directory was removed. */
+function deletedCwdError(): NodeJS.ErrnoException {
+  return Object.assign(
+    new Error(
+      "ENOENT: process.cwd failed with error no such file or directory, the current working directory was likely removed without changing the working directory, uv_cwd"
+    ),
+    { code: "ENOENT", errno: -2, syscall: "uv_cwd" }
+  );
+}
+
+afterEach(() => {
+  vi.restoreAllMocks();
+  vi.unstubAllEnvs();
+});
+
+describe("buildContext cwd", () => {
+  test("falls back to PWD when the working directory was deleted", () => {
+    vi.spyOn(process, "cwd").mockImplementation(() => {
+      throw deletedCwdError();
+    });
+    vi.stubEnv("PWD", "/tmp/removed-worktree");
+
+    const context = buildContext(process);
+
+    expect(context.cwd).toBe("/tmp/removed-worktree");
+    expect(context.forCommand({ prefix: ["sentry"] }).cwd).toBe(
+      "/tmp/removed-worktree"
+    );
+  });
+
+  test("rethrows when PWD cannot stand in for the working directory", () => {
+    const error = deletedCwdError();
+    vi.spyOn(process, "cwd").mockImplementation(() => {
+      throw error;
+    });
+
+    vi.stubEnv("PWD", "");
+    expect(() => buildContext(process)).toThrow(error);
+
+    vi.stubEnv("PWD", "relative/dir");
+    expect(() => buildContext(process)).toThrow(error);
+  });
+});