diff --git a/src/commands/cli/upgrade.ts b/src/commands/cli/upgrade.ts
index f046b9ff8..81f9ecde1 100644
--- a/src/commands/cli/upgrade.ts
+++ b/src/commands/cli/upgrade.ts
@@ -46,6 +46,7 @@ import {
   getCurlInstallPaths,
   type InstallationMethod,
   NIGHTLY_TAG,
+  type OfflineMode,
   parseInstallationMethod,
   VERSION_PREFIX_REGEX,
   versionExists,
@@ -163,7 +164,7 @@ async function resolveTargetWithFallback(opts: {
    *  clearing the version cache before the offline path can read it). */
   persistChannelFn: () => void;
 }): Promise<
-  | { kind: "target"; target: string; offline: boolean }
+  | { kind: "target"; target: string; offline: OfflineMode }
   | { kind: "done"; result: UpgradeResult }
 > {
   const { resolveOpts, versionArg, offline, method, persistChannelFn } = opts;
@@ -183,7 +184,7 @@ async function resolveTargetWithFallback(opts: {
     const target = resolveOfflineTarget(versionArg);
     persistChannelFn();
     log.info(`Offline mode: using cached target ${target}`);
-    return { kind: "target", target, offline: true };
+    return { kind: "target", target, offline: "explicit" };
   }
 
   // Non-offline: persist channel upfront (no cache dependency)
@@ -209,7 +210,7 @@ async function resolveTargetWithFallback(opts: {
       const target = resolveOfflineTarget(versionArg);
       log.warn("Network unavailable, falling back to cached upgrade target");
       log.info(`Using cached target: ${target}`);
-      return { kind: "target", target, offline: true };
+      return { kind: "target", target, offline: "network-fallback" };
     } catch {
       // No cached version either — re-throw original network error
       throw error;
@@ -427,7 +428,7 @@ async function executeStandardUpgrade(opts: {
   versionArg: string | undefined;
   target: string;
   execPath: string;
-  offline?: boolean;
+  offline?: OfflineMode;
   json?: boolean;
 }): Promise<void> {
   const { method, channel, versionArg, target, execPath, offline, json } = opts;
@@ -608,7 +609,7 @@ function startChangelogFetch(
   channel: ReleaseChannel,
   currentVersion: string,
   targetVersion: string,
-  offline: boolean
+  offline: OfflineMode
 ): Promise<ChangelogSummary | undefined> {
   if (offline || currentVersion === targetVersion) {
     return Promise.resolve(undefined);
@@ -631,7 +632,7 @@ async function buildCheckResultWithChangelog(opts: {
   method: InstallationMethod;
   channel: ReleaseChannel;
   flags: UpgradeFlags;
-  offline: boolean;
+  offline: OfflineMode;
   changelogPromise: Promise<ChangelogSummary | undefined>;
 }): Promise<UpgradeResult> {
   const result = buildCheckResult(opts);
@@ -776,7 +777,7 @@ export const upgradeCommand = buildCommand({
         channel,
         method,
         forced: false,
-        offline: offline || undefined,
+        offline: offline ? true : undefined,
       } satisfies UpgradeResult);
     }
     const downgrade = isDowngrade(CLI_VERSION, target);
@@ -813,7 +814,7 @@ export const upgradeCommand = buildCommand({
       channel,
       method,
       forced: flags.force,
-      offline: offline || undefined,
+      offline: offline ? true : undefined,
       warnings,
       changelog,
     } satisfies UpgradeResult);
diff --git a/src/lib/errors.ts b/src/lib/errors.ts
index 502267092..7e058a051 100644
--- a/src/lib/errors.ts
+++ b/src/lib/errors.ts
@@ -392,7 +392,8 @@ export type UpgradeErrorReason =
   | "unsupported_operation"
   | "network_error"
   | "execution_failed"
-  | "version_not_found";
+  | "version_not_found"
+  | "offline_cache_miss";
 
 /**
  * Upgrade-related errors.
@@ -412,6 +413,8 @@ export class UpgradeError extends CliError {
       network_error: "Failed to fetch version information.",
       execution_failed: "Upgrade command failed.",
       version_not_found: "The specified version was not found.",
+      offline_cache_miss:
+        "Cannot upgrade offline — no pre-downloaded update is available.",
     };
     super(message ?? defaultMessages[reason]);
     this.name = "UpgradeError";
diff --git a/src/lib/upgrade.ts b/src/lib/upgrade.ts
index 0b6a4ed2c..62760722f 100644
--- a/src/lib/upgrade.ts
+++ b/src/lib/upgrade.ts
@@ -57,6 +57,15 @@ export type InstallationMethod =
 /** Package managers that can be used for global installs */
 type PackageManager = "npm" | "pnpm" | "bun" | "yarn";
 
+/**
+ * How the current upgrade reached the offline code path.
+ *
+ * - `false` — online upgrade (network available)
+ * - `"explicit"` — user passed `--offline` flag
+ * - `"network-fallback"` — network failed, auto-fell back to cache
+ */
+export type OfflineMode = false | "explicit" | "network-fallback";
+
 // Constants
 
 /** The git tag used for the rolling nightly GitHub release (stable fallback only). */
@@ -680,7 +689,7 @@ async function downloadStableToPath(
 export async function downloadBinaryToTemp(
   version: string,
   downloadTag?: string,
-  offline?: boolean
+  offline?: OfflineMode
 ): Promise<DownloadResult> {
   const { tempPath, lockPath } = getCurlInstallPaths();
 
@@ -696,14 +705,18 @@ export async function downloadBinaryToTemp(
 
     // Try delta upgrade first — downloads tiny patches instead of full binary.
     // Falls back to full download on any failure (missing patches, hash mismatch, etc.)
-    const deltaResult = await tryDeltaUpgrade(version, tempPath, offline);
+    const deltaResult = await tryDeltaUpgrade(version, tempPath, !!offline);
     let patchBytes: number | undefined;
     if (deltaResult) {
       patchBytes = deltaResult.patchBytes;
     } else if (offline) {
       throw new UpgradeError(
-        "network_error",
-        `No cached patches available for upgrade to ${version}. Run 'sentry cli upgrade' with network access first.`
+        "offline_cache_miss",
+        offline === "explicit"
+          ? `Cannot upgrade to ${version} in offline mode — no pre-downloaded update is available. ` +
+              "Run `sentry cli upgrade` without `--offline` to download the update directly."
+          : `Cannot upgrade to ${version} — the network is unavailable and no pre-downloaded update was found. ` +
+              "Check your internet connection and try again."
       );
     } else {
       log.debug("Downloading full binary");
@@ -875,7 +888,7 @@ export async function executeUpgrade(
   method: InstallationMethod,
   version: string,
   downloadTag?: string,
-  offline?: boolean
+  offline?: OfflineMode
 ): Promise<DownloadResult | null> {
   switch (method) {
     case "curl":
diff --git a/test/lib/upgrade.test.ts b/test/lib/upgrade.test.ts
index b843f6d79..6179090d1 100644
--- a/test/lib/upgrade.test.ts
+++ b/test/lib/upgrade.test.ts
@@ -25,6 +25,7 @@ import { UpgradeError } from "../../src/lib/errors.js";
 import {
   detectInstallationMethod,
   detectPackageManagerFromPath,
+  downloadBinaryToTemp,
   executeUpgrade,
   fetchLatestFromGitHub,
   fetchLatestFromNpm,
@@ -270,6 +271,14 @@ describe("UpgradeError", () => {
     );
   });
 
+  test("creates error with default message for offline_cache_miss", () => {
+    const error = new UpgradeError("offline_cache_miss");
+    expect(error.reason).toBe("offline_cache_miss");
+    expect(error.message).toBe(
+      "Cannot upgrade offline — no pre-downloaded update is available."
+    );
+  });
+
   test("allows custom message", () => {
     const error = new UpgradeError("network_error", "Custom error message");
     expect(error.reason).toBe("network_error");
@@ -1471,3 +1480,64 @@ describe("executeUpgrade with curl method (nightly)", () => {
     expect(new Uint8Array(content)).toEqual(mockBinaryContent);
   });
 });
+
+describe("downloadBinaryToTemp offline errors", () => {
+  const offlineBinDir = join(TEST_TMP_DIR, "upgrade-offline-test");
+  const offlineInstallPath = join(offlineBinDir, "sentry");
+
+  beforeEach(() => {
+    clearInstallInfo();
+    mkdirSync(offlineBinDir, { recursive: true });
+    setInstallInfo({
+      method: "curl",
+      path: offlineInstallPath,
+      version: "0.0.0",
+    });
+  });
+
+  afterEach(async () => {
+    globalThis.fetch = originalFetch;
+    const paths = getCurlInstallPaths();
+    for (const p of [
+      paths.installPath,
+      paths.tempPath,
+      paths.oldPath,
+      paths.lockPath,
+    ]) {
+      try {
+        await unlink(p);
+      } catch {
+        // Ignore
+      }
+    }
+    clearInstallInfo();
+  });
+
+  test("explicit offline: throws offline_cache_miss with actionable message", async () => {
+    try {
+      await downloadBinaryToTemp("0.26.1", undefined, "explicit");
+      expect.unreachable("Should have thrown");
+    } catch (error) {
+      expect(error).toBeInstanceOf(UpgradeError);
+      const upgradeError = error as UpgradeError;
+      expect(upgradeError.reason).toBe("offline_cache_miss");
+      expect(upgradeError.message).toContain("in offline mode");
+      expect(upgradeError.message).toContain("without `--offline`");
+      expect(upgradeError.message).not.toContain("cached patches");
+    }
+  });
+
+  test("network fallback: throws offline_cache_miss with connection message", async () => {
+    try {
+      await downloadBinaryToTemp("0.26.1", undefined, "network-fallback");
+      expect.unreachable("Should have thrown");
+    } catch (error) {
+      expect(error).toBeInstanceOf(UpgradeError);
+      const upgradeError = error as UpgradeError;
+      expect(upgradeError.reason).toBe("offline_cache_miss");
+      expect(upgradeError.message).toContain("network is unavailable");
+      expect(upgradeError.message).toContain("Check your internet connection");
+      expect(upgradeError.message).not.toContain("cached patches");
+    }
+  });
+});