diff --git a/CHANGELOG.md b/CHANGELOG.md
index f2271eb46..0ae254e4d 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -10,7 +10,7 @@
 
 ### Fixes
 - Embedded runner: suppress raw API error payloads from replies. (#924) — thanks @grp06.
-- Slack: respect `channels.slack.requireMention` default when resolving channel mention gating. (#850) — thanks @evalexpr.
+- Auth: normalize Claude Code CLI profile mode to oauth and auto-migrate config. (#855) — thanks @sebslight.
 
 ## 2026.1.14
 
diff --git a/src/agents/auth-profiles.resolve-auth-profile-order.does-not-prioritize-lastgood-round-robin-ordering.test.ts b/src/agents/auth-profiles.resolve-auth-profile-order.does-not-prioritize-lastgood-round-robin-ordering.test.ts
index dbb4355a9..692b67a01 100644
--- a/src/agents/auth-profiles.resolve-auth-profile-order.does-not-prioritize-lastgood-round-robin-ordering.test.ts
+++ b/src/agents/auth-profiles.resolve-auth-profile-order.does-not-prioritize-lastgood-round-robin-ordering.test.ts
@@ -154,4 +154,81 @@ describe("resolveAuthProfileOrder", () => {
     });
     expect(order).toEqual(["anthropic:work", "anthropic:default"]);
   });
+
+  it("mode: oauth config accepts both oauth and token credentials (issue #559)", () => {
+    const now = Date.now();
+    const storeWithBothTypes: AuthProfileStore = {
+      version: 1,
+      profiles: {
+        "anthropic:oauth-cred": {
+          type: "oauth",
+          provider: "anthropic",
+          access: "access-token",
+          refresh: "refresh-token",
+          expires: now + 60_000,
+        },
+        "anthropic:token-cred": {
+          type: "token",
+          provider: "anthropic",
+          token: "just-a-token",
+          expires: now + 60_000,
+        },
+      },
+    };
+
+    const orderOauthCred = resolveAuthProfileOrder({
+      store: storeWithBothTypes,
+      provider: "anthropic",
+      cfg: {
+        auth: {
+          profiles: {
+            "anthropic:oauth-cred": { provider: "anthropic", mode: "oauth" },
+          },
+        },
+      },
+    });
+    expect(orderOauthCred).toContain("anthropic:oauth-cred");
+
+    const orderTokenCred = resolveAuthProfileOrder({
+      store: storeWithBothTypes,
+      provider: "anthropic",
+      cfg: {
+        auth: {
+          profiles: {
+            "anthropic:token-cred": { provider: "anthropic", mode: "oauth" },
+          },
+        },
+      },
+    });
+    expect(orderTokenCred).toContain("anthropic:token-cred");
+  });
+
+  it("mode: token config rejects oauth credentials (issue #559 root cause)", () => {
+    const now = Date.now();
+    const storeWithOauth: AuthProfileStore = {
+      version: 1,
+      profiles: {
+        "anthropic:oauth-cred": {
+          type: "oauth",
+          provider: "anthropic",
+          access: "access-token",
+          refresh: "refresh-token",
+          expires: now + 60_000,
+        },
+      },
+    };
+
+    const order = resolveAuthProfileOrder({
+      store: storeWithOauth,
+      provider: "anthropic",
+      cfg: {
+        auth: {
+          profiles: {
+            "anthropic:oauth-cred": { provider: "anthropic", mode: "token" },
+          },
+        },
+      },
+    });
+    expect(order).not.toContain("anthropic:oauth-cred");
+  });
 });
diff --git a/src/commands/auth-choice.apply.anthropic.ts b/src/commands/auth-choice.apply.anthropic.ts
index b85b4bb9c..64678e51c 100644
--- a/src/commands/auth-choice.apply.anthropic.ts
+++ b/src/commands/auth-choice.apply.anthropic.ts
@@ -84,7 +84,7 @@ export async function applyAuthChoiceAnthropic(
     nextConfig = applyAuthProfileConfig(nextConfig, {
       profileId: CLAUDE_CLI_PROFILE_ID,
       provider: "anthropic",
-      mode: "token",
+      mode: "oauth",
     });
     return { config: nextConfig };
   }
@@ -146,7 +146,7 @@ export async function applyAuthChoiceAnthropic(
     nextConfig = applyAuthProfileConfig(nextConfig, {
       profileId: CLAUDE_CLI_PROFILE_ID,
       provider: "anthropic",
-      mode: "token",
+      mode: "oauth",
     });
     return { config: nextConfig };
   }
diff --git a/src/commands/models/auth.ts b/src/commands/models/auth.ts
index ca0830a09..0b11f1e68 100644
--- a/src/commands/models/auth.ts
+++ b/src/commands/models/auth.ts
@@ -91,12 +91,12 @@ export async function modelsAuthSetupTokenCommand(
     applyAuthProfileConfig(cfg, {
       profileId: CLAUDE_CLI_PROFILE_ID,
       provider: "anthropic",
-      mode: "token",
+      mode: "oauth",
     }),
   );
 
   runtime.log(`Updated ${CONFIG_PATH_CLAWDBOT}`);
-  runtime.log(`Auth profile: ${CLAUDE_CLI_PROFILE_ID} (anthropic/token)`);
+  runtime.log(`Auth profile: ${CLAUDE_CLI_PROFILE_ID} (anthropic/oauth)`);
 }
 
 export async function modelsAuthPasteTokenCommand(
diff --git a/src/commands/onboard-non-interactive/local/auth-choice.ts b/src/commands/onboard-non-interactive/local/auth-choice.ts
index 3c2786264..65cf83bec 100644
--- a/src/commands/onboard-non-interactive/local/auth-choice.ts
+++ b/src/commands/onboard-non-interactive/local/auth-choice.ts
@@ -270,7 +270,7 @@ export async function applyNonInteractiveAuthChoice(params: {
     return applyAuthProfileConfig(nextConfig, {
       profileId: CLAUDE_CLI_PROFILE_ID,
       provider: "anthropic",
-      mode: "token",
+      mode: "oauth",
     });
   }
 
diff --git a/src/config/config.legacy-config-detection.accepts-imessage-dmpolicy.test.ts b/src/config/config.legacy-config-detection.accepts-imessage-dmpolicy.test.ts
index 9379fba72..eb6c8ce2f 100644
--- a/src/config/config.legacy-config-detection.accepts-imessage-dmpolicy.test.ts
+++ b/src/config/config.legacy-config-detection.accepts-imessage-dmpolicy.test.ts
@@ -200,6 +200,46 @@ describe("legacy config detection", () => {
       }
     });
   });
+  it("auto-migrates claude-cli auth profile mode to oauth", async () => {
+    await withTempHome(async (home) => {
+      const configPath = path.join(home, ".clawdbot", "clawdbot.json");
+      await fs.mkdir(path.dirname(configPath), { recursive: true });
+      await fs.writeFile(
+        configPath,
+        JSON.stringify(
+          {
+            auth: {
+              profiles: {
+                "anthropic:claude-cli": { provider: "anthropic", mode: "token" },
+              },
+            },
+          },
+          null,
+          2,
+        ),
+        "utf-8",
+      );
+
+      const warnSpy = vi.spyOn(console, "warn").mockImplementation(() => {});
+      vi.resetModules();
+      try {
+        const { loadConfig } = await import("./config.js");
+        const cfg = loadConfig();
+        expect(cfg.auth?.profiles?.["anthropic:claude-cli"]?.mode).toBe("oauth");
+
+        const raw = await fs.readFile(configPath, "utf-8");
+        const parsed = JSON.parse(raw) as {
+          auth?: { profiles?: Record<string, { mode?: string }> };
+        };
+        expect(parsed.auth?.profiles?.["anthropic:claude-cli"]?.mode).toBe("oauth");
+        expect(
+          warnSpy.mock.calls.some(([msg]) => String(msg).includes("Auto-migrated config")),
+        ).toBe(true);
+      } finally {
+        warnSpy.mockRestore();
+      }
+    });
+  });
   it("auto-migrates legacy provider sections on load and writes back", async () => {
     await withTempHome(async (home) => {
       const configPath = path.join(home, ".clawdbot", "clawdbot.json");
diff --git a/src/config/legacy.migrations.part-3.ts b/src/config/legacy.migrations.part-3.ts
index 6831f8335..1f38fe42e 100644
--- a/src/config/legacy.migrations.part-3.ts
+++ b/src/config/legacy.migrations.part-3.ts
@@ -10,6 +10,20 @@ import {
 } from "./legacy.shared.js";
 
 export const LEGACY_CONFIG_MIGRATIONS_PART_3: LegacyConfigMigration[] = [
+  {
+    id: "auth.anthropic-claude-cli-mode-oauth",
+    describe: "Switch anthropic:claude-cli auth profile mode to oauth",
+    apply: (raw, changes) => {
+      const auth = getRecord(raw.auth);
+      const profiles = getRecord(auth?.profiles);
+      if (!profiles) return;
+      const claudeCli = getRecord(profiles["anthropic:claude-cli"]);
+      if (!claudeCli) return;
+      if (claudeCli.mode !== "token") return;
+      claudeCli.mode = "oauth";
+      changes.push('Updated auth.profiles["anthropic:claude-cli"].mode → "oauth".');
+    },
+  },
   {
     id: "agent.defaults-v2",
     describe: "Move agent config to agents.defaults and tools",