diff --git a/packages/cli/package.json b/packages/cli/package.json
index da3dfa5f..8052e8d1 100644
--- a/packages/cli/package.json
+++ b/packages/cli/package.json
@@ -1,6 +1,6 @@
 {
   "name": "@openrouter/spawn",
-  "version": "0.16.1",
+  "version": "0.16.2",
   "type": "module",
   "bin": {
     "spawn": "cli.js"
diff --git a/packages/cli/src/__tests__/result-helpers.test.ts b/packages/cli/src/__tests__/result-helpers.test.ts
new file mode 100644
index 00000000..adb49e89
--- /dev/null
+++ b/packages/cli/src/__tests__/result-helpers.test.ts
@@ -0,0 +1,326 @@
+import { describe, expect, it } from "bun:test";
+import {
+  asyncTryCatch,
+  asyncTryCatchIf,
+  Err,
+  isFileError,
+  isNetworkError,
+  isOperationalError,
+  mapResult,
+  Ok,
+  tryCatch,
+  tryCatchIf,
+  unwrapOr,
+} from "../shared/result";
+
+// ── Helper: create an Error with a `code` property (like Node.js errno errors) ──
+
+function errnoError(message: string, code: string): Error {
+  const err = new Error(message);
+  Object.defineProperty(err, "code", {
+    value: code,
+  });
+  return err;
+}
+
+// ── tryCatch ────────────────────────────────────────────────────────────────────
+
+describe("tryCatch", () => {
+  it("returns Ok on success", () => {
+    const result = tryCatch(() => 42);
+    expect(result.ok).toBe(true);
+    if (result.ok) {
+      expect(result.data).toBe(42);
+    }
+  });
+
+  it("returns Err on thrown Error", () => {
+    const result = tryCatch(() => {
+      throw new Error("boom");
+    });
+    expect(result.ok).toBe(false);
+    if (!result.ok) {
+      expect(result.error.message).toBe("boom");
+    }
+  });
+
+  it("wraps non-Error throws in Error", () => {
+    const result = tryCatch(() => {
+      throw "string error";
+    });
+    expect(result.ok).toBe(false);
+    if (!result.ok) {
+      expect(result.error.message).toBe("string error");
+    }
+  });
+});
+
+// ── asyncTryCatch ───────────────────────────────────────────────────────────────
+
+describe("asyncTryCatch", () => {
+  it("returns Ok on resolved promise", async () => {
+    const result = await asyncTryCatch(async () => "hello");
+    expect(result.ok).toBe(true);
+    if (result.ok) {
+      expect(result.data).toBe("hello");
+    }
+  });
+
+  it("returns Err on rejected promise", async () => {
+    const result = await asyncTryCatch(async () => {
+      throw new Error("async boom");
+    });
+    expect(result.ok).toBe(false);
+    if (!result.ok) {
+      expect(result.error.message).toBe("async boom");
+    }
+  });
+
+  it("returns Err on sync throw inside async fn", async () => {
+    const result = await asyncTryCatch(() => Promise.reject(new Error("rejected")));
+    expect(result.ok).toBe(false);
+    if (!result.ok) {
+      expect(result.error.message).toBe("rejected");
+    }
+  });
+});
+
+// ── tryCatchIf ──────────────────────────────────────────────────────────────────
+
+describe("tryCatchIf", () => {
+  it("returns Ok on success", () => {
+    const result = tryCatchIf(isFileError, () => 42);
+    expect(result.ok).toBe(true);
+    if (result.ok) {
+      expect(result.data).toBe(42);
+    }
+  });
+
+  it("returns Err when guard matches", () => {
+    const result = tryCatchIf(isFileError, () => {
+      throw errnoError("file not found", "ENOENT");
+    });
+    expect(result.ok).toBe(false);
+    if (!result.ok) {
+      expect(result.error.message).toBe("file not found");
+    }
+  });
+
+  it("re-throws when guard does NOT match", () => {
+    expect(() => {
+      tryCatchIf(isFileError, () => {
+        throw new TypeError("cannot read property of null");
+      });
+    }).toThrow(TypeError);
+  });
+
+  it("re-throws RangeError (programming bug)", () => {
+    expect(() => {
+      tryCatchIf(isFileError, () => {
+        throw new RangeError("index out of range");
+      });
+    }).toThrow(RangeError);
+  });
+});
+
+// ── asyncTryCatchIf ─────────────────────────────────────────────────────────────
+
+describe("asyncTryCatchIf", () => {
+  it("returns Ok on success", async () => {
+    const result = await asyncTryCatchIf(isNetworkError, async () => "ok");
+    expect(result.ok).toBe(true);
+    if (result.ok) {
+      expect(result.data).toBe("ok");
+    }
+  });
+
+  it("returns Err when guard matches", async () => {
+    const result = await asyncTryCatchIf(isNetworkError, async () => {
+      throw errnoError("connection refused", "ECONNREFUSED");
+    });
+    expect(result.ok).toBe(false);
+    if (!result.ok) {
+      expect(result.error.message).toBe("connection refused");
+    }
+  });
+
+  it("re-throws when guard does NOT match", async () => {
+    await expect(
+      asyncTryCatchIf(isNetworkError, async () => {
+        throw new TypeError("null dereference");
+      }),
+    ).rejects.toThrow(TypeError);
+  });
+});
+
+// ── unwrapOr ────────────────────────────────────────────────────────────────────
+
+describe("unwrapOr", () => {
+  it("returns data on Ok", () => {
+    expect(unwrapOr(Ok(42), 0)).toBe(42);
+  });
+
+  it("returns fallback on Err", () => {
+    expect(unwrapOr(Err(new Error("fail")), 0)).toBe(0);
+  });
+
+  it("returns null fallback on Err", () => {
+    const result: string | null = unwrapOr(Err(new Error("fail")), null);
+    expect(result).toBeNull();
+  });
+});
+
+// ── mapResult ───────────────────────────────────────────────────────────────────
+
+describe("mapResult", () => {
+  it("transforms Ok value", () => {
+    const result = mapResult(Ok(5), (n) => n * 2);
+    expect(result.ok).toBe(true);
+    if (result.ok) {
+      expect(result.data).toBe(10);
+    }
+  });
+
+  it("passes Err through unchanged", () => {
+    const err = new Error("fail");
+    const result = mapResult(Err<number>(err), (n) => n * 2);
+    expect(result.ok).toBe(false);
+    if (!result.ok) {
+      expect(result.error).toBe(err);
+    }
+  });
+});
+
+// ── isFileError ─────────────────────────────────────────────────────────────────
+
+describe("isFileError", () => {
+  it("returns true for ENOENT", () => {
+    expect(isFileError(errnoError("no such file", "ENOENT"))).toBe(true);
+  });
+
+  it("returns true for EACCES", () => {
+    expect(isFileError(errnoError("permission denied", "EACCES"))).toBe(true);
+  });
+
+  it("returns true for EISDIR", () => {
+    expect(isFileError(errnoError("is a directory", "EISDIR"))).toBe(true);
+  });
+
+  it("returns true for ENOSPC", () => {
+    expect(isFileError(errnoError("no space left", "ENOSPC"))).toBe(true);
+  });
+
+  it("returns false for TypeError", () => {
+    expect(isFileError(new TypeError("cannot read"))).toBe(false);
+  });
+
+  it("returns false for generic Error", () => {
+    expect(isFileError(new Error("something"))).toBe(false);
+  });
+
+  it("returns false for network error code", () => {
+    expect(isFileError(errnoError("conn refused", "ECONNREFUSED"))).toBe(false);
+  });
+});
+
+// ── isNetworkError ──────────────────────────────────────────────────────────────
+
+describe("isNetworkError", () => {
+  it("returns true for ECONNREFUSED", () => {
+    expect(isNetworkError(errnoError("conn refused", "ECONNREFUSED"))).toBe(true);
+  });
+
+  it("returns true for ECONNRESET", () => {
+    expect(isNetworkError(errnoError("conn reset", "ECONNRESET"))).toBe(true);
+  });
+
+  it("returns true for ETIMEDOUT", () => {
+    expect(isNetworkError(errnoError("timed out", "ETIMEDOUT"))).toBe(true);
+  });
+
+  it("returns true for AbortError", () => {
+    const err = new Error("aborted");
+    err.name = "AbortError";
+    expect(isNetworkError(err)).toBe(true);
+  });
+
+  it("returns true for TimeoutError", () => {
+    const err = new Error("timed out");
+    err.name = "TimeoutError";
+    expect(isNetworkError(err)).toBe(true);
+  });
+
+  it('returns true for "fetch failed" message', () => {
+    expect(isNetworkError(new Error("fetch failed"))).toBe(true);
+  });
+
+  it('returns true for "network error" message', () => {
+    expect(isNetworkError(new Error("network error"))).toBe(true);
+  });
+
+  it("returns true for TypeError with fetch message", () => {
+    expect(isNetworkError(new TypeError("fetch failed: connection refused"))).toBe(true);
+  });
+
+  it("returns false for TypeError without network message", () => {
+    expect(isNetworkError(new TypeError("cannot read property of null"))).toBe(false);
+  });
+
+  it("returns false for generic Error", () => {
+    expect(isNetworkError(new Error("something else"))).toBe(false);
+  });
+
+  it("returns false for file error code", () => {
+    expect(isNetworkError(errnoError("no such file", "ENOENT"))).toBe(false);
+  });
+});
+
+// ── isOperationalError ──────────────────────────────────────────────────────────
+
+describe("isOperationalError", () => {
+  it("returns true for file errors", () => {
+    expect(isOperationalError(errnoError("no such file", "ENOENT"))).toBe(true);
+  });
+
+  it("returns true for network errors", () => {
+    expect(isOperationalError(errnoError("conn refused", "ECONNREFUSED"))).toBe(true);
+  });
+
+  it("returns false for TypeError", () => {
+    expect(isOperationalError(new TypeError("bug"))).toBe(false);
+  });
+
+  it("returns false for RangeError", () => {
+    expect(isOperationalError(new RangeError("out of range"))).toBe(false);
+  });
+});
+
+// ── Bug propagation integration test ────────────────────────────────────────────
+
+describe("bug propagation", () => {
+  it("TypeError from null dereference is NOT caught by tryCatchIf(isFileError)", () => {
+    expect(() => {
+      tryCatchIf(isFileError, () => {
+        // Simulate a programming bug — accessing a property on null throws TypeError
+        const obj: Record<string, unknown> | null = null;
+        return obj!.foo;
+      });
+    }).toThrow(TypeError);
+  });
+
+  it("SyntaxError is NOT caught by tryCatchIf(isFileError)", () => {
+    expect(() => {
+      tryCatchIf(isFileError, () => {
+        JSON.parse("not valid json {{{");
+      });
+    }).toThrow(SyntaxError);
+  });
+
+  it("RangeError is NOT caught by tryCatchIf(isNetworkError)", () => {
+    expect(() => {
+      tryCatchIf(isNetworkError, () => {
+        throw new RangeError("maximum call stack size exceeded");
+      });
+    }).toThrow(RangeError);
+  });
+});
diff --git a/packages/cli/src/aws/aws.ts b/packages/cli/src/aws/aws.ts
index abe24749..215e59ea 100644
--- a/packages/cli/src/aws/aws.ts
+++ b/packages/cli/src/aws/aws.ts
@@ -10,6 +10,7 @@ import { handleBillingError, isBillingError, showNonBillingError } from "../shar
 import { getPackagesForTier, NODE_INSTALL_CMD, needsBun, needsNode } from "../shared/cloud-init";
 import { parseJsonWith } from "../shared/parse";
 import { getSpawnCloudConfigPath } from "../shared/paths";
+import { isFileError, tryCatchIf, unwrapOr } from "../shared/result.js";
 import {
   killWithTimeout,
   SSH_BASE_OPTS,
@@ -68,26 +69,27 @@ export function loadCredsFromConfig(): {
   secretAccessKey: string;
   region: string;
 } | null {
-  try {
-    const raw = readFileSync(getAwsConfigPath(), "utf-8");
-    const data = parseJsonWith(raw, AwsCredsSchema);
-    if (!data?.accessKeyId || !data?.secretAccessKey) {
-      return null;
-    }
-    if (!/^[A-Za-z0-9/+]{16,128}$/.test(data.accessKeyId)) {
-      return null;
-    }
-    if (data.secretAccessKey.length < 16) {
-      return null;
-    }
-    return {
-      accessKeyId: data.accessKeyId,
-      secretAccessKey: data.secretAccessKey,
-      region: data.region || "us-east-1",
-    };
-  } catch {
-    return null;
-  }
+  return unwrapOr(
+    tryCatchIf(isFileError, () => {
+      const raw = readFileSync(getAwsConfigPath(), "utf-8");
+      const data = parseJsonWith(raw, AwsCredsSchema);
+      if (!data?.accessKeyId || !data?.secretAccessKey) {
+        return null;
+      }
+      if (!/^[A-Za-z0-9/+]{16,128}$/.test(data.accessKeyId)) {
+        return null;
+      }
+      if (data.secretAccessKey.length < 16) {
+        return null;
+      }
+      return {
+        accessKeyId: data.accessKeyId,
+        secretAccessKey: data.secretAccessKey,
+        region: data.region || "us-east-1",
+      };
+    }),
+    null,
+  );
 }
 
 // ─── Lightsail Bundles ────────────────────────────────────────────────────────
diff --git a/packages/cli/src/digitalocean/digitalocean.ts b/packages/cli/src/digitalocean/digitalocean.ts
index 2d5f975c..9cdf524b 100644
--- a/packages/cli/src/digitalocean/digitalocean.ts
+++ b/packages/cli/src/digitalocean/digitalocean.ts
@@ -9,6 +9,7 @@ import { getPackagesForTier, NODE_INSTALL_CMD, needsBun, needsNode } from "../sh
 import { OAUTH_CSS } from "../shared/oauth";
 import { parseJsonObj } from "../shared/parse";
 import { getSpawnCloudConfigPath } from "../shared/paths";
+import { asyncTryCatchIf, isFileError, isNetworkError, tryCatchIf, unwrapOr } from "../shared/result.js";
 import {
   killWithTimeout,
   SSH_BASE_OPTS,
@@ -152,7 +153,8 @@ async function doApi(method: string, endpoint: string, body?: string, maxRetries
       }
       return text;
     } catch (err) {
-      if (attempt >= maxRetries) {
+      const e = err instanceof Error ? err : new Error(String(err));
+      if (!isNetworkError(e) || attempt >= maxRetries) {
         throw err;
       }
       logWarn(`API request failed (attempt ${attempt}/${maxRetries}), retrying...`);
@@ -166,11 +168,10 @@ async function doApi(method: string, endpoint: string, body?: string, maxRetries
 // ─── Token Persistence ───────────────────────────────────────────────────────
 
 function loadConfig(): Record<string, unknown> | null {
-  try {
-    return parseJsonObj(readFileSync(getSpawnCloudConfigPath("digitalocean"), "utf-8"));
-  } catch {
-    return null;
-  }
+  return unwrapOr(
+    tryCatchIf(isFileError, () => parseJsonObj(readFileSync(getSpawnCloudConfigPath("digitalocean"), "utf-8"))),
+    null,
+  );
 }
 
 async function saveConfig(values: Record<string, unknown>): Promise<void> {
@@ -234,12 +235,13 @@ async function testDoToken(): Promise<boolean> {
   if (!_state.token) {
     return false;
   }
-  try {
-    const text = await doApi("GET", "/account", undefined, 1);
-    return text.includes('"uuid"');
-  } catch {
-    return false;
-  }
+  return unwrapOr(
+    await asyncTryCatchIf(isNetworkError, async () => {
+      const text = await doApi("GET", "/account", undefined, 1);
+      return text.includes('"uuid"');
+    }),
+    false,
+  );
 }
 
 /**
diff --git a/packages/cli/src/hetzner/hetzner.ts b/packages/cli/src/hetzner/hetzner.ts
index c9eaf1a8..e586a1d9 100644
--- a/packages/cli/src/hetzner/hetzner.ts
+++ b/packages/cli/src/hetzner/hetzner.ts
@@ -8,6 +8,7 @@ import { handleBillingError, isBillingError, showNonBillingError } from "../shar
 import { getPackagesForTier, NODE_INSTALL_CMD, needsBun, needsNode } from "../shared/cloud-init";
 import { parseJsonObj } from "../shared/parse";
 import { getSpawnCloudConfigPath } from "../shared/paths";
+import { asyncTryCatchIf, isNetworkError, unwrapOr } from "../shared/result.js";
 import {
   killWithTimeout,
   SSH_BASE_OPTS,
@@ -99,7 +100,8 @@ async function hetznerApi(method: string, endpoint: string, body?: string, maxRe
       }
       return text;
     } catch (err) {
-      if (attempt >= maxRetries) {
+      const e = err instanceof Error ? err : new Error(String(err));
+      if (!isNetworkError(e) || attempt >= maxRetries) {
         throw err;
       }
       logWarn(`API request failed (attempt ${attempt}/${maxRetries}), retrying...`);
@@ -131,19 +133,20 @@ async function testHcloudToken(): Promise<boolean> {
   if (!_state.hcloudToken) {
     return false;
   }
-  try {
-    const resp = await hetznerApi("GET", "/servers?per_page=1", undefined, 1);
-    const data = parseJsonObj(resp);
-    // Hetzner returns { "error": { ... } } on auth failure.
-    // Success responses may contain "error": null inside action objects,
-    // so check for a real error object with a message.
-    if (toRecord(data?.error)?.message) {
-      return false;
-    }
-    return true;
-  } catch {
-    return false;
-  }
+  return unwrapOr(
+    await asyncTryCatchIf(isNetworkError, async () => {
+      const resp = await hetznerApi("GET", "/servers?per_page=1", undefined, 1);
+      const data = parseJsonObj(resp);
+      // Hetzner returns { "error": { ... } } on auth failure.
+      // Success responses may contain "error": null inside action objects,
+      // so check for a real error object with a message.
+      if (toRecord(data?.error)?.message) {
+        return false;
+      }
+      return true;
+    }),
+    false,
+  );
 }
 
 // ─── Authentication ──────────────────────────────────────────────────────────
diff --git a/packages/cli/src/history.ts b/packages/cli/src/history.ts
index 03e96884..4d3b167f 100644
--- a/packages/cli/src/history.ts
+++ b/packages/cli/src/history.ts
@@ -12,7 +12,7 @@ import {
 import { join } from "node:path";
 import * as v from "valibot";
 import { getHistoryPath, getSpawnDir } from "./shared/paths.js";
-import { tryCatch } from "./shared/result.js";
+import { isFileError, tryCatch, tryCatchIf } from "./shared/result.js";
 import { getErrorMessage } from "./shared/type-guards.js";
 import { logDebug, logWarn } from "./shared/ui.js";
 
@@ -101,7 +101,7 @@ function writeHistory(records: SpawnRecord[]): void {
 /** Save launch command to a history record's connection.
  *  Matches by spawnId when provided; falls back to most recent record with a connection. */
 export function saveLaunchCmd(launchCmd: string, spawnId?: string): void {
-  const result = tryCatch(() => {
+  const result = tryCatchIf(isFileError, () => {
     const history = loadHistory();
     let found = false;
 
@@ -135,7 +135,7 @@ export function saveLaunchCmd(launchCmd: string, spawnId?: string): void {
 
 /** Back up a corrupted file before discarding it. Non-fatal (best-effort). */
 function backupCorruptedFile(filePath: string): void {
-  const result = tryCatch(() => {
+  const result = tryCatchIf(isFileError, () => {
     copyFileSync(filePath, `${filePath}.corrupt.${Date.now()}`);
     console.error(`Warning: ${filePath} was corrupted. A backup has been saved with .corrupt suffix.`);
   });
@@ -144,7 +144,8 @@ function backupCorruptedFile(filePath: string): void {
   }
 }
 
-/** Try to parse valid records from a single archive file. */
+/** Try to parse valid records from a single archive file.
+ *  Uses tryCatch (catch-all) because corrupted JSON is expected — SyntaxError is not a file error. */
 function parseArchiveFile(dir: string, file: string): SpawnRecord[] | null {
   const result = tryCatch(() => {
     const text = readFileSync(join(dir, file), "utf-8");
@@ -160,7 +161,8 @@ function parseArchiveFile(dir: string, file: string): SpawnRecord[] | null {
   return result.data.length > 0 ? result.data : null;
 }
 
-/** Attempt to recover records from archive files (history-*.json). */
+/** Attempt to recover records from archive files (history-*.json).
+ *  Uses tryCatch (catch-all) because archive recovery is best-effort — any failure returns []. */
 function recoverFromArchives(): SpawnRecord[] {
   const result = tryCatch(() => {
     const dir = getSpawnDir();
@@ -214,7 +216,7 @@ export function loadHistory(): SpawnRecord[] {
   if (!existsSync(path)) {
     return [];
   }
-  const readResult = tryCatch(() => readFileSync(path, "utf-8"));
+  const readResult = tryCatchIf(isFileError, () => readFileSync(path, "utf-8"));
   if (!readResult.ok) {
     logWarn("Could not read spawn history");
     logDebug(getErrorMessage(readResult.error));
@@ -263,7 +265,7 @@ function archiveRecords(records: SpawnRecord[]): void {
     return;
   }
   // Non-fatal — archive failure should not block saving
-  tryCatch(() => {
+  tryCatchIf(isFileError, () => {
     const dir = getSpawnDir();
     const date = new Date().toISOString().slice(0, 10);
     const archivePath = join(dir, `history-${date}.json`);
diff --git a/packages/cli/src/manifest.ts b/packages/cli/src/manifest.ts
index d48fdf36..ed09267b 100644
--- a/packages/cli/src/manifest.ts
+++ b/packages/cli/src/manifest.ts
@@ -1,6 +1,7 @@
 import { existsSync, mkdirSync, readFileSync, statSync, writeFileSync } from "node:fs";
 import { join } from "node:path";
 import { getCacheDir, getCacheFile } from "./shared/paths.js";
+import { asyncTryCatch, isFileError, tryCatchIf, unwrapOr } from "./shared/result.js";
 import { getErrorMessage } from "./shared/type-guards.js";
 
 // ── Types ──────────────────────────────────────────────────────────────────────
@@ -78,13 +79,13 @@ const FETCH_TIMEOUT = 10_000; // 10 seconds
 // ── Cache helpers ──────────────────────────────────────────────────────────────
 
 function cacheAge(): number {
-  try {
-    const st: ReturnType<typeof statSync> = statSync(getCacheFile());
-    return (Date.now() - st.mtimeMs) / 1000;
-  } catch (_err) {
-    // Cache file doesn't exist or is inaccessible - treat as infinitely old
-    return Number.POSITIVE_INFINITY;
-  }
+  return unwrapOr(
+    tryCatchIf(isFileError, () => {
+      const st: ReturnType<typeof statSync> = statSync(getCacheFile());
+      return (Date.now() - st.mtimeMs) / 1000;
+    }),
+    Number.POSITIVE_INFINITY,
+  );
 }
 
 function logError(message: string, err?: unknown): void {
@@ -92,18 +93,19 @@ function logError(message: string, err?: unknown): void {
 }
 
 function readCache(): Manifest | null {
-  try {
+  const result = tryCatchIf(isFileError, () => {
     const raw = JSON.parse(readFileSync(getCacheFile(), "utf-8"));
     const cleaned = stripDangerousKeys(raw);
     if (isValidManifest(cleaned)) {
       return cleaned;
     }
     return null;
-  } catch (err) {
-    // Cache file missing, corrupted, or unreadable
-    logError(`Failed to read cache from ${getCacheFile()}`, err);
+  });
+  if (!result.ok) {
+    logError(`Failed to read cache from ${getCacheFile()}`, result.error);
     return null;
   }
+  return result.data;
 }
 
 function isTestEnv(): boolean {
@@ -159,7 +161,9 @@ function isValidManifest(data: unknown): data is Manifest {
 }
 
 async function fetchManifestFromGitHub(): Promise<Manifest | null> {
-  try {
+  // Uses asyncTryCatch (catch-all) because fetch + JSON parse + validation is a single
+  // remote operation — any failure (network, JSON parse, TypeError) means "fetch failed".
+  const result = await asyncTryCatch(async () => {
     const res = await fetch(`${RAW_BASE}/manifest.json`, {
       signal: AbortSignal.timeout(FETCH_TIMEOUT),
     });
@@ -174,10 +178,12 @@ async function fetchManifestFromGitHub(): Promise<Manifest | null> {
       return null;
     }
     return data;
-  } catch (err) {
-    logError("Network error fetching manifest", err);
+  });
+  if (!result.ok) {
+    logError("Network error fetching manifest", result.error);
     return null;
   }
+  return result.data;
 }
 
 // ── Public API ─────────────────────────────────────────────────────────────────
@@ -205,8 +211,7 @@ function tryLoadLocalManifest(): Manifest | null {
     return null;
   }
 
-  try {
-    // Try loading manifest.json from current directory (development mode)
+  const result = tryCatchIf(isFileError, () => {
     const localPath = join(process.cwd(), "manifest.json");
     if (existsSync(localPath)) {
       const raw = JSON.parse(readFileSync(localPath, "utf-8"));
@@ -215,10 +220,9 @@ function tryLoadLocalManifest(): Manifest | null {
         return data;
       }
     }
-  } catch (_err) {
-    // Local manifest not found or invalid - not an error, just continue
-  }
-  return null;
+    return null;
+  });
+  return result.ok ? result.data : null;
 }
 
 export async function loadManifest(forceRefresh = false): Promise<Manifest> {
diff --git a/packages/cli/src/shared/agent-setup.ts b/packages/cli/src/shared/agent-setup.ts
index 477324b1..238ddefa 100644
--- a/packages/cli/src/shared/agent-setup.ts
+++ b/packages/cli/src/shared/agent-setup.ts
@@ -7,6 +7,7 @@ import type { Result } from "./ui";
 import { unlinkSync, writeFileSync } from "node:fs";
 import { join } from "node:path";
 import { getTmpDir } from "./paths";
+import { asyncTryCatchIf, isOperationalError, tryCatchIf } from "./result.js";
 import { getErrorMessage } from "./type-guards";
 import { Err, jsonEscape, logError, logInfo, logStep, logWarn, Ok, withRetry } from "./ui";
 
@@ -170,8 +171,8 @@ let hostGitEmail = "";
 
 /** Read a git config value from the host machine, returning "" on failure. */
 function readHostGitConfig(key: string): string {
-  try {
-    const result = Bun.spawnSync(
+  const result = tryCatchIf(isOperationalError, () => {
+    const r = Bun.spawnSync(
       [
         "git",
         "config",
@@ -186,21 +187,20 @@ function readHostGitConfig(key: string): string {
         ],
       },
     );
-    if (result.exitCode === 0) {
-      return new TextDecoder().decode(result.stdout).trim();
+    if (r.exitCode === 0) {
+      return new TextDecoder().decode(r.stdout).trim();
     }
-  } catch {
-    /* ignore — git may not be installed on host */
-  }
-  return "";
+    return "";
+  });
+  return result.ok ? result.data : "";
 }
 
 async function detectGithubAuth(): Promise<void> {
   if (process.env.GITHUB_TOKEN) {
     githubToken = process.env.GITHUB_TOKEN;
   } else {
-    try {
-      const result = Bun.spawnSync(
+    const ghResult = tryCatchIf(isOperationalError, () => {
+      const r = Bun.spawnSync(
         [
           "gh",
           "auth",
@@ -214,11 +214,13 @@ async function detectGithubAuth(): Promise<void> {
           ],
         },
       );
-      if (result.exitCode === 0) {
-        githubToken = new TextDecoder().decode(result.stdout).trim();
+      if (r.exitCode === 0) {
+        return new TextDecoder().decode(r.stdout).trim();
       }
-    } catch {
-      /* ignore */
+      return "";
+    });
+    if (ghResult.ok && ghResult.data) {
+      githubToken = ghResult.data;
     }
   }
 
@@ -246,9 +248,8 @@ export async function offerGithubAuth(runner: CloudRunner): Promise<void> {
   }
 
   logStep("Installing and authenticating GitHub CLI on the remote server...");
-  try {
-    await runner.runServer(ghCmd);
-  } catch {
+  const ghSetup = await asyncTryCatchIf(isOperationalError, () => runner.runServer(ghCmd));
+  if (!ghSetup.ok) {
     logWarn("GitHub CLI setup failed (non-fatal, continuing)");
   }
 
@@ -264,10 +265,10 @@ export async function offerGithubAuth(runner: CloudRunner): Promise<void> {
       const escaped = hostGitEmail.replace(/'/g, "'\\''");
       cmds.push(`git config --global user.email '${escaped}'`);
     }
-    try {
-      await runner.runServer(cmds.join(" && "));
+    const gitSetup = await asyncTryCatchIf(isOperationalError, () => runner.runServer(cmds.join(" && ")));
+    if (gitSetup.ok) {
       logInfo("Git identity configured on remote server");
-    } catch {
+    } else {
       logWarn("Git identity setup failed (non-fatal, continuing)");
     }
   }
@@ -296,16 +297,18 @@ async function installChromeBrowser(runner: CloudRunner): Promise<void> {
   // Snap Chromium on Ubuntu 24.04 fails — AppArmor confinement blocks CDP control.
   // Google Chrome .deb bypasses snap entirely and lands at /usr/bin/google-chrome.
   logStep("Installing Google Chrome for browser tool...");
-  try {
-    await runner.runServer(
+  const result = await asyncTryCatchIf(isOperationalError, () =>
+    runner.runServer(
       "{ command -v google-chrome-stable >/dev/null 2>&1 || command -v google-chrome >/dev/null 2>&1; } && { echo 'Chrome already installed'; exit 0; }; " +
         "curl --proto '=https' -fsSL https://dl.google.com/linux/direct/google-chrome-stable_current_amd64.deb -o /tmp/google-chrome.deb && " +
         "sudo dpkg -i /tmp/google-chrome.deb; sudo apt-get install -f -y -qq; " +
         "rm -f /tmp/google-chrome.deb",
       120,
-    );
+    ),
+  );
+  if (result.ok) {
     logInfo("Google Chrome installed");
-  } catch {
+  } else {
     logWarn("Google Chrome install failed (browser tool will be unavailable)");
   }
 }
@@ -354,15 +357,16 @@ async function setupOpenclawConfig(
 
   // Configure browser via CLI (openclaw config set) — the supported way to set
   // browser options. Writing JSON directly may not be picked up by all versions.
-  try {
-    await runner.runServer(
+  const browserResult = await asyncTryCatchIf(isOperationalError, () =>
+    runner.runServer(
       "export PATH=$HOME/.npm-global/bin:$HOME/.bun/bin:$HOME/.local/bin:$PATH; " +
         "openclaw config set browser.executablePath /usr/bin/google-chrome-stable; " +
         "openclaw config set browser.noSandbox true; " +
         "openclaw config set browser.headless true; " +
         "openclaw config set browser.defaultProfile openclaw",
-    );
-  } catch {
+    ),
+  );
+  if (!browserResult.ok) {
     logWarn("Browser config setup failed (non-fatal)");
   }
 
@@ -527,10 +531,10 @@ async function ensureSwapSpace(runner: CloudRunner, sizeMb = 1024): Promise<void
     "  echo '==> Swap enabled'",
     "fi",
   ].join("\n");
-  try {
-    await runner.runServer(script);
+  const result = await asyncTryCatchIf(isOperationalError, () => runner.runServer(script));
+  if (result.ok) {
     logInfo("Swap space ready");
-  } catch {
+  } else {
     logWarn("Swap setup failed (non-fatal) — build may still succeed on larger instances");
   }
 }
diff --git a/packages/cli/src/shared/oauth.ts b/packages/cli/src/shared/oauth.ts
index e4e56e4e..9608d81d 100644
--- a/packages/cli/src/shared/oauth.ts
+++ b/packages/cli/src/shared/oauth.ts
@@ -6,6 +6,7 @@ import * as v from "valibot";
 import { OAUTH_CODE_REGEX } from "./oauth-constants";
 import { parseJsonWith } from "./parse";
 import { getSpawnCloudConfigPath } from "./paths";
+import { asyncTryCatchIf, isFileError, isNetworkError, tryCatchIf } from "./result.js";
 import { getErrorMessage, isString } from "./type-guards";
 import { logDebug, logError, logInfo, logStep, logWarn, openBrowser, prompt } from "./ui";
 
@@ -25,7 +26,7 @@ async function verifyOpenrouterKey(apiKey: string): Promise<boolean> {
     return true;
   }
 
-  try {
+  const result = await asyncTryCatchIf(isNetworkError, async () => {
     const resp = await fetch("https://openrouter.ai/api/v1/auth/key", {
       headers: {
         Authorization: `Bearer ${apiKey}`,
@@ -41,9 +42,8 @@ async function verifyOpenrouterKey(apiKey: string): Promise<boolean> {
       return false;
     }
     return true; // unknown status = don't block
-  } catch {
-    return true; // network error = skip validation
-  }
+  });
+  return result.ok ? result.data : true; // network error = skip validation
 }
 
 // ─── OAuth Flow via Bun.serve ────────────────────────────────────────────────
@@ -67,12 +67,14 @@ async function tryOauthFlow(callbackPort = 5180, agentSlug?: string, cloudSlug?:
   logStep("Attempting OAuth authentication...");
 
   // Check network connectivity
-  try {
+  const reachable = await asyncTryCatchIf(isNetworkError, async () => {
     await fetch("https://openrouter.ai", {
       method: "HEAD",
       signal: AbortSignal.timeout(5_000),
     });
-  } catch {
+    return true;
+  });
+  if (!reachable.ok) {
     logWarn("Cannot reach openrouter.ai — network may be unavailable");
     return null;
   }
@@ -191,7 +193,7 @@ async function tryOauthFlow(callbackPort = 5180, agentSlug?: string, cloudSlug?:
 
   // Exchange code for API key
   logStep("Exchanging OAuth code for API key...");
-  try {
+  const exchangeResult = await asyncTryCatchIf(isNetworkError, async () => {
     const resp = await fetch("https://openrouter.ai/api/v1/auth/keys", {
       method: "POST",
       headers: {
@@ -209,17 +211,19 @@ async function tryOauthFlow(callbackPort = 5180, agentSlug?: string, cloudSlug?:
     }
     logError("Failed to exchange OAuth code for API key");
     return null;
-  } catch (_err) {
+  });
+  if (!exchangeResult.ok) {
     logError("Failed to contact OpenRouter API");
     return null;
   }
+  return exchangeResult.data;
 }
 
 // ─── API Key Persistence ─────────────────────────────────────────────────────
 
 /** Save OpenRouter API key to ~/.config/spawn/openrouter.json so it persists across runs. */
 async function saveOpenRouterKey(key: string): Promise<void> {
-  try {
+  const result = await asyncTryCatchIf(isFileError, async () => {
     const configPath = getSpawnCloudConfigPath("openrouter");
     mkdirSync(dirname(configPath), {
       recursive: true,
@@ -238,15 +242,16 @@ async function saveOpenRouterKey(key: string): Promise<void> {
         mode: 0o600,
       },
     );
-  } catch (err) {
+  });
+  if (!result.ok) {
     logWarn("Could not save API key — you may need to re-authenticate next run");
-    logDebug(getErrorMessage(err));
+    logDebug(getErrorMessage(result.error));
   }
 }
 
 /** Load a previously saved OpenRouter API key from ~/.config/spawn/openrouter.json. */
 function loadSavedOpenRouterKey(): string | null {
-  try {
+  const result = tryCatchIf(isFileError, () => {
     const configPath = getSpawnCloudConfigPath("openrouter");
     const data = JSON.parse(readFileSync(configPath, "utf-8"));
     const key = isString(data.api_key) ? data.api_key : "";
@@ -254,9 +259,8 @@ function loadSavedOpenRouterKey(): string | null {
       return key;
     }
     return null;
-  } catch {
-    return null;
-  }
+  });
+  return result.ok ? result.data : null;
 }
 
 // ─── Main API Key Acquisition ────────────────────────────────────────────────
diff --git a/packages/cli/src/shared/orchestrate.ts b/packages/cli/src/shared/orchestrate.ts
index 0f47c6d3..c2340e02 100644
--- a/packages/cli/src/shared/orchestrate.ts
+++ b/packages/cli/src/shared/orchestrate.ts
@@ -11,6 +11,7 @@ import { offerGithubAuth, wrapSshCall } from "./agent-setup";
 import { tryTarballInstall } from "./agent-tarball";
 import { generateEnvConfig } from "./agents";
 import { getOrPromptApiKey } from "./oauth";
+import { asyncTryCatchIf, isOperationalError } from "./result.js";
 import { startSshTunnel } from "./ssh";
 import { ensureSshKeys, getSshKeyOpts } from "./ssh-keys";
 import { getErrorMessage } from "./type-guards";
@@ -89,6 +90,7 @@ export async function runOrchestration(
   await cloud.authenticate();
 
   // 1b. Pre-flight account readiness check (billing, email verification, etc.)
+  //     Uses try/catch (not guarded) because hooks can throw ANY provider-specific error.
   if (cloud.checkAccountReady) {
     try {
       await cloud.checkAccountReady();
@@ -103,6 +105,7 @@ export async function runOrchestration(
   const apiKey = await getOrPromptApiKey(agentName, cloud.cloudName);
 
   // 3. Pre-provision hooks (e.g., GitHub auth prompt — non-fatal)
+  //     Uses try/catch (not guarded) because hooks can throw ANY provider-specific error.
   if (agent.preProvision) {
     try {
       await agent.preProvision();
@@ -214,7 +217,7 @@ export async function runOrchestration(
   if (agent.tunnel) {
     if (cloud.getConnectionInfo) {
       // SSH-based cloud: tunnel the remote port to localhost
-      try {
+      const tunnelResult = await asyncTryCatchIf(isOperationalError, async () => {
         const conn = cloud.getConnectionInfo();
         const keys = await ensureSshKeys();
         tunnelHandle = await startSshTunnel({
@@ -229,7 +232,8 @@ export async function runOrchestration(
             openBrowser(url);
           }
         }
-      } catch {
+      });
+      if (!tunnelResult.ok) {
         logWarn("Web dashboard tunnel failed — use the TUI instead");
       }
     } else if (cloud.cloudName === "local") {
diff --git a/packages/cli/src/shared/result.ts b/packages/cli/src/shared/result.ts
index b384c139..f8547bdc 100644
--- a/packages/cli/src/shared/result.ts
+++ b/packages/cli/src/shared/result.ts
@@ -1 +1,14 @@
-export { Err, Ok, type Result, tryCatch } from "@openrouter/spawn-shared";
+export {
+  asyncTryCatch,
+  asyncTryCatchIf,
+  Err,
+  isFileError,
+  isNetworkError,
+  isOperationalError,
+  mapResult,
+  Ok,
+  type Result,
+  tryCatch,
+  tryCatchIf,
+  unwrapOr,
+} from "@openrouter/spawn-shared";
diff --git a/packages/cli/src/shared/ui.ts b/packages/cli/src/shared/ui.ts
index 1591d579..1fff0afc 100644
--- a/packages/cli/src/shared/ui.ts
+++ b/packages/cli/src/shared/ui.ts
@@ -4,6 +4,7 @@
 import { readFileSync } from "node:fs";
 import * as p from "@clack/prompts";
 import { getSpawnCloudConfigPath } from "./paths";
+import { isFileError, tryCatchIf, unwrapOr } from "./result.js";
 import { isString } from "./type-guards";
 
 const RED = "\x1b[0;31m";
@@ -232,19 +233,20 @@ export async function withRetry<T>(
  * Returns null if the file is missing, unreadable, or the token is invalid.
  */
 export function loadApiToken(cloud: string): string | null {
-  try {
-    const data = JSON.parse(readFileSync(getSpawnCloudConfigPath(cloud), "utf-8"));
-    const token = (isString(data.api_key) ? data.api_key : "") || (isString(data.token) ? data.token : "");
-    if (!token) {
-      return null;
-    }
-    if (!/^[a-zA-Z0-9._/@:+=, -]+$/.test(token)) {
-      return null;
-    }
-    return token;
-  } catch {
-    return null;
-  }
+  return unwrapOr(
+    tryCatchIf(isFileError, () => {
+      const data = JSON.parse(readFileSync(getSpawnCloudConfigPath(cloud), "utf-8"));
+      const token = (isString(data.api_key) ? data.api_key : "") || (isString(data.token) ? data.token : "");
+      if (!token) {
+        return null;
+      }
+      if (!/^[a-zA-Z0-9._/@:+=, -]+$/.test(token)) {
+        return null;
+      }
+      return token;
+    }),
+    null,
+  );
 }
 
 /** JSON-escape a string (returns the quoted JSON string). */
diff --git a/packages/cli/src/update-check.ts b/packages/cli/src/update-check.ts
index 0002c6a8..aa77e067 100644
--- a/packages/cli/src/update-check.ts
+++ b/packages/cli/src/update-check.ts
@@ -9,6 +9,7 @@ import pkg from "../package.json" with { type: "json" };
 import { RAW_BASE, SPAWN_CDN, VERSION_URL } from "./manifest.js";
 import { PkgVersionSchema, parseJsonWith } from "./shared/parse";
 import { getUpdateFailedPath } from "./shared/paths";
+import { asyncTryCatchIf, isFileError, isNetworkError, tryCatchIf, unwrapOr } from "./shared/result";
 import { getErrorMessage, hasStatus } from "./shared/type-guards";
 import { logDebug, logWarn } from "./shared/ui";
 
@@ -33,7 +34,7 @@ const CROSS_MARK = isAscii ? "x" : "\u2717";
 
 async function fetchLatestVersion(): Promise<string | null> {
   // Primary: plain-text version file from GitHub release artifact (static URL)
-  try {
+  const primary = await asyncTryCatchIf(isNetworkError, async () => {
     const res = await fetch(VERSION_URL, {
       signal: AbortSignal.timeout(FETCH_TIMEOUT),
     });
@@ -43,12 +44,14 @@ async function fetchLatestVersion(): Promise<string | null> {
         return text;
       }
     }
-  } catch {
-    // Fall through to GitHub raw fallback
+    return null;
+  });
+  if (primary.ok && primary.data) {
+    return primary.data;
   }
 
   // Fallback: package.json from GitHub raw
-  try {
+  const fallback = await asyncTryCatchIf(isNetworkError, async () => {
     const res = await fetch(`${RAW_BASE}/packages/cli/package.json`, {
       signal: AbortSignal.timeout(FETCH_TIMEOUT),
     });
@@ -57,9 +60,8 @@ async function fetchLatestVersion(): Promise<string | null> {
     }
     const data = parseJsonWith(await res.text(), PkgVersionSchema);
     return data?.version ?? null;
-  } catch {
-    return null;
-  }
+  });
+  return fallback.ok ? fallback.data : null;
 }
 
 function compareVersions(current: string, latest: string): boolean {
@@ -84,37 +86,34 @@ function compareVersions(current: string, latest: string): boolean {
 // ── Failure Backoff ──────────────────────────────────────────────────────────
 
 function isUpdateBackedOff(): boolean {
-  try {
-    const failedPath = getUpdateFailedPath();
-    const content = fs.readFileSync(failedPath, "utf8").trim();
-    const failedAt = Number.parseInt(content, 10);
-    if (Number.isNaN(failedAt)) {
-      return false;
-    }
-    return Date.now() - failedAt < UPDATE_BACKOFF_MS;
-  } catch {
-    return false;
-  }
+  return unwrapOr(
+    tryCatchIf(isFileError, () => {
+      const failedPath = getUpdateFailedPath();
+      const content = fs.readFileSync(failedPath, "utf8").trim();
+      const failedAt = Number.parseInt(content, 10);
+      if (Number.isNaN(failedAt)) {
+        return false;
+      }
+      return Date.now() - failedAt < UPDATE_BACKOFF_MS;
+    }),
+    false,
+  );
 }
 
 function markUpdateFailed(): void {
-  try {
+  tryCatchIf(isFileError, () => {
     const failedPath = getUpdateFailedPath();
     fs.mkdirSync(path.dirname(failedPath), {
       recursive: true,
     });
     fs.writeFileSync(failedPath, String(Date.now()));
-  } catch {
-    // Best-effort — don't break the CLI if we can't write the file
-  }
+  });
 }
 
 function clearUpdateFailed(): void {
-  try {
+  tryCatchIf(isFileError, () => {
     fs.unlinkSync(getUpdateFailedPath());
-  } catch {
-    // File may not exist — that's fine
-  }
+  });
 }
 
 /** Print boxed update banner to stderr */
diff --git a/packages/shared/src/index.ts b/packages/shared/src/index.ts
index 0390ebd3..6455c968 100644
--- a/packages/shared/src/index.ts
+++ b/packages/shared/src/index.ts
@@ -1,3 +1,16 @@
 export { parseJsonObj, parseJsonWith } from "./parse";
-export { Err, Ok, type Result, tryCatch } from "./result";
+export {
+  asyncTryCatch,
+  asyncTryCatchIf,
+  Err,
+  isFileError,
+  isNetworkError,
+  isOperationalError,
+  mapResult,
+  Ok,
+  type Result,
+  tryCatch,
+  tryCatchIf,
+  unwrapOr,
+} from "./result";
 export { getErrorMessage, hasStatus, isNumber, isString, toObjectArray, toRecord } from "./type-guards";
diff --git a/packages/shared/src/result.ts b/packages/shared/src/result.ts
index 2ed9fbd8..d3c83186 100644
--- a/packages/shared/src/result.ts
+++ b/packages/shared/src/result.ts
@@ -31,3 +31,107 @@ export function tryCatch<T>(fn: () => T): Result<T> {
     return Err(e instanceof Error ? e : new Error(String(e)));
   }
 }
+
+/** Wrap an async function call into a Result — no try/catch at the call site. */
+export async function asyncTryCatch<T>(fn: () => Promise<T>): Promise<Result<T>> {
+  try {
+    return Ok(await fn());
+  } catch (e) {
+    return Err(e instanceof Error ? e : new Error(String(e)));
+  }
+}
+
+/**
+ * Guarded sync try/catch — catches ONLY errors where `guard` returns true.
+ * Non-matching errors (programming bugs like TypeError) are re-thrown immediately.
+ */
+export function tryCatchIf<T>(guard: (err: Error) => boolean, fn: () => T): Result<T> {
+  try {
+    return Ok(fn());
+  } catch (e) {
+    const err = e instanceof Error ? e : new Error(String(e));
+    if (guard(err)) {
+      return Err(err);
+    }
+    throw e;
+  }
+}
+
+/**
+ * Guarded async try/catch — catches ONLY errors where `guard` returns true.
+ * Non-matching errors (programming bugs like TypeError) are re-thrown immediately.
+ */
+export async function asyncTryCatchIf<T>(guard: (err: Error) => boolean, fn: () => Promise<T>): Promise<Result<T>> {
+  try {
+    return Ok(await fn());
+  } catch (e) {
+    const err = e instanceof Error ? e : new Error(String(e));
+    if (guard(err)) {
+      return Err(err);
+    }
+    throw e;
+  }
+}
+
+/** Extract the value from a Result, returning `fallback` on Err. */
+export function unwrapOr<T>(result: Result<T>, fallback: T): T {
+  return result.ok ? result.data : fallback;
+}
+
+/** Transform the Ok value of a Result, passing Err through unchanged. */
+export function mapResult<T, U>(result: Result<T>, fn: (data: T) => U): Result<U> {
+  return result.ok ? Ok(fn(result.data)) : result;
+}
+
+// ── Error predicates ──────────────────────────────────────────────────────────
+
+const FILE_ERROR_CODES = new Set([
+  "ENOENT",
+  "EACCES",
+  "EISDIR",
+  "ENOSPC",
+  "EPERM",
+  "ENOTDIR",
+]);
+
+/** Returns true for filesystem I/O errors (ENOENT, EACCES, EISDIR, ENOSPC, EPERM, ENOTDIR). */
+export function isFileError(err: Error): boolean {
+  const code = (err as NodeJS.ErrnoException).code;
+  return typeof code === "string" && FILE_ERROR_CODES.has(code);
+}
+
+const NETWORK_ERROR_CODES = new Set([
+  "ECONNREFUSED",
+  "ECONNRESET",
+  "ETIMEDOUT",
+  "ENOTFOUND",
+  "EPIPE",
+  "EAI_AGAIN",
+]);
+
+/** Returns true for network/fetch errors (connection refused, reset, timeout, DNS, AbortError, "fetch failed"). */
+export function isNetworkError(err: Error): boolean {
+  const code = (err as NodeJS.ErrnoException).code;
+  if (typeof code === "string" && NETWORK_ERROR_CODES.has(code)) {
+    return true;
+  }
+  if (err.name === "AbortError" || err.name === "TimeoutError") {
+    return true;
+  }
+  // Bun throws TypeError on fetch failures; also match common error message patterns
+  if (err.name === "TypeError" && /fetch|network|socket/i.test(err.message)) {
+    return true;
+  }
+  const msg = err.message.toLowerCase();
+  return (
+    msg.includes("fetch failed") ||
+    msg.includes("network error") ||
+    msg.includes("econnrefused") ||
+    msg.includes("econnreset")
+  );
+}
+
+/** Returns true for operational errors (file I/O + network) — safe broad default for non-fatal catches. */
+export function isOperationalError(err: Error): boolean {
+  return isFileError(err) || isNetworkError(err);
+}