diff --git a/packages/cli/src/cli.ts b/packages/cli/src/cli.ts
index afc2547d8..d12f595c5 100644
--- a/packages/cli/src/cli.ts
+++ b/packages/cli/src/cli.ts
@@ -631,24 +631,27 @@ export async function runCli(
     const { resolveCommandPath } = await import("./lib/introspect.js");
     const { getDefaultOrganization } = await import("./lib/db/defaults.js");
 
+    // Redact first: a sensitive flag's value would otherwise survive as a
+    // path segment or the trailing argv token.
+    const safeArgv = redactArgv(argv);
+
     // Strip flags so resolveCommandPath only sees command path segments
-    const pathSegments = argv.filter((t) => !t.startsWith("-"));
+    const pathSegments = safeArgv.filter((t) => !t.startsWith("-"));
     const resolved = resolveCommandPath(
       routes as unknown as Parameters<typeof resolveCommandPath>[0],
       pathSegments,
     );
     const unknownToken =
-      resolved?.kind === "unresolved" ? resolved.input : (argv.at(-1) ?? "");
+      resolved?.kind === "unresolved"
+        ? resolved.input
+        : (safeArgv.at(-1) ?? "");
     const suggestions =
       resolved?.kind === "unresolved" ? resolved.suggestions : [];
 
     // Extract org/project from argv, fall back to default org from SQLite
-    const fromArgv = extractOrgProjectFromArgv(argv);
+    const fromArgv = extractOrgProjectFromArgv(safeArgv);
     const org = fromArgv.org ?? getDefaultOrganization() ?? undefined;
 
-    // Redact sensitive flags (e.g., --token) before sending to Sentry
-    const safeArgv = redactArgv(argv);
-
     Sentry.setTag("command", "unknown");
     if (org) {
       Sentry.setTag("sentry.org", org);
@@ -660,7 +663,7 @@ export async function runCli(
       argv: safeArgv,
       unknown_token: unknownToken,
       suggestions,
-      arg_count: argv.length,
+      arg_count: safeArgv.length,
       org: org ?? null,
       project: fromArgv.project ?? null,
     });
diff --git a/packages/cli/test/lib/unknown-command-telemetry.test.ts b/packages/cli/test/lib/unknown-command-telemetry.test.ts
new file mode 100644
index 000000000..8d9b6df29
--- /dev/null
+++ b/packages/cli/test/lib/unknown-command-telemetry.test.ts
@@ -0,0 +1,47 @@
+// oxlint-disable-next-line sentry-cli/no-namespace-import -- needed for spyOn
+import * as Sentry from "@sentry/node";
+import { afterEach, beforeEach, describe, expect, test, vi } from "vitest";
+import { runCli } from "../../src/cli.js";
+import { SENTRY_CLI } from "../../src/sentry-cli.js";
+import { useTestConfigDir } from "../helpers.js";
+
+useTestConfigDir("unknown-command-telemetry-");
+
+const SECRET = "abcd12efg0";
+const originalExitCode = process.exitCode;
+
+let setContextSpy: ReturnType<typeof vi.spyOn>;
+
+beforeEach(() => {
+  vi.spyOn(process.stdout, "write").mockReturnValue(true);
+  vi.spyOn(process.stderr, "write").mockReturnValue(true);
+  setContextSpy = vi.spyOn(Sentry, "setContext");
+});
+
+afterEach(() => {
+  vi.restoreAllMocks();
+  process.exitCode = originalExitCode;
+});
+
+describe("unknown_command telemetry: sensitive flag values are redacted", () => {
+  test.each([
+    {
+      label: "--flag VALUE form",
+      argv: ["alert", "--token", SECRET],
+    },
+    {
+      label: "--flag=VALUE form",
+      argv: ["alert", `--token=${SECRET}`],
+    },
+  ])("$label does not leak the token", async ({ argv }) => {
+    await runCli(argv, SENTRY_CLI);
+
+    const unknownCommandCall = setContextSpy.mock.calls.find(
+      ([name]) => name === "unknown_command",
+    );
+    expect(unknownCommandCall).toBeDefined();
+
+    const serialized = JSON.stringify(unknownCommandCall);
+    expect(serialized).not.toContain(SECRET);
+  });
+});