feat(setup): Anthropic OAuth onboarding with setup-token support (#384)

* feat(setup): add Anthropic OAuth and Codex OAuth onboarding flows

Add OAuth token authentication as an alternative to API keys during
onboarding for both Anthropic (via `claude login`) and OpenAI/Codex
(via `~/.codex/auth.json`).

Key changes:
- New `AnthropicOAuthProvider` using `Authorization: Bearer` header
  (rig-core hardcodes `x-api-key` which rejects OAuth tokens)
- Wizard auth method selector: "Direct API Key" vs "OAuth Token"
  for both Anthropic and OpenAI providers
- Codex token extraction from `$CODEX_HOME/auth.json` / `~/.codex/auth.json`
- Claude Code sandbox sub-step in Docker setup (checks for credentials)
- Secret injection mappings for `ANTHROPIC_OAUTH_TOKEN` and `CODEX_OAUTH_TOKEN`
- `CODEX_OAUTH_TOKEN` falls back to `OPENAI_API_KEY` (same Bearer auth)

Supersedes #143 which had a broken auth flow (OAuth token sent as
x-api-key → 401). Credit to @bigguybobby for the original approach.

Co-Authored-By: Claude Opus 4.6 <[email protected]>

* fix: persist OAuth tokens in bootstrap .env and re-extract at startup

OAuth tokens stored only in the secrets DB were invisible to
Config::from_env() which runs before the DB connects (chicken-and-egg).

Two fixes:
1. write_bootstrap_env() now persists ANTHROPIC_OAUTH_TOKEN and
   CODEX_OAUTH_TOKEN to ~/.ironclaw/.env (same pattern as NEARAI_API_KEY)
2. main.rs re-extracts a fresh token from the OS credential store
   (macOS Keychain / ~/.claude/.credentials.json) before config resolution,
   handling token expiry (8-12h) gracefully

Co-Authored-By: Claude Opus 4.6 <[email protected]>

* fix: persist all LLM credentials in bootstrap .env, not just NEAR AI

All providers had the same chicken-and-egg issue: API keys stored in the
secrets DB were invisible to Config::from_env() which runs before DB
connects. Only NEARAI_API_KEY was written to bootstrap .env.

Now write_bootstrap_env() persists all credential env vars:
NEARAI_API_KEY, ANTHROPIC_API_KEY, ANTHROPIC_OAUTH_TOKEN, OPENAI_API_KEY,
CODEX_OAUTH_TOKEN, LLM_API_KEY, TINFOIL_API_KEY.

Also: setup_api_key_provider() now sets the env var during the wizard
session so write_bootstrap_env() can pick it up.

Co-Authored-By: Claude Opus 4.6 <[email protected]>

* fix: address security review findings for OAuth onboarding

- Extract "oauth-placeholder" to named OAUTH_PLACEHOLDER constant shared
  across config and wizard to prevent silent drift
- Document plaintext credential tradeoff in write_bootstrap_env (API keys
  stored with 0o600 permissions, recommend full-disk encryption)
- Add blocking "Press Enter" wait in Anthropic OAuth retry flow so user
  has time to run `claude login` in another terminal
- Add escape hatch from manual OAuth paste back to API key flow (empty
  input switches to setup_api_key_provider)
- Fix Retry-After header: parse u64 seconds into Duration before passing
  to LlmError::RateLimited
- Make config::llm module pub(crate) for constant visibility
- Use .bearer_auth() instead of manual format!("Bearer {}")
- Remove response body from debug log (may contain PII)
- Update Anthropic API version to 2024-10-22

Co-Authored-By: Claude Opus 4.6 <[email protected]>

* security: remove plaintext credentials from bootstrap .env

Credentials (API keys, OAuth tokens) were being written in plaintext to
~/.ironclaw/.env to work around a chicken-and-egg problem: Config::from_env()
runs before the encrypted secrets DB is connected.

Instead of storing secrets on disk, LlmConfig::resolve() now defers
gracefully when credentials are missing — it returns None for the provider
config instead of hard-erroring with MissingRequired. After the DB connects,
AppBuilder::build_all() loads secrets from encrypted storage via
inject_llm_keys_from_secrets() and re-resolves the config.

For Anthropic OAuth tokens (which expire in 8-12h), the secret injection
step also tries the OS credential store (macOS Keychain / Linux
credentials.json) for a fresh token, overriding the potentially stale
copy in the DB.

Changes:
- LlmConfig::resolve(): OpenAI, Anthropic, OpenAI-compatible, and Tinfoil
  all return None instead of MissingRequired when credentials are absent
- write_bootstrap_env(): no longer writes any credential env vars
- inject_llm_keys_from_secrets(): refreshes Anthropic OAuth from OS
  credential store before overlay is finalized
- main.rs: removed OAuth re-extraction hack (no longer needed)

Co-Authored-By: Claude Opus 4.6 <[email protected]>

* fix: load OS credential store tokens even without secrets DB

The OAuth token extraction from macOS Keychain / Linux credentials files
was only running inside inject_llm_keys_from_secrets(), which requires
the encrypted secrets DB. When no master key is configured, init_secrets()
returned early — skipping both DB secret loading AND OS credential store
extraction, leaving the Anthropic OAuth token unavailable.

Split into two paths:
- inject_llm_keys_from_secrets(): loads from encrypted DB + OS stores
- inject_os_credentials(): loads from OS stores only (no DB needed)

init_secrets() now calls inject_os_credentials() and re-resolves config
even in the no-master-key early-return path, so `claude login` tokens
are always available regardless of secrets DB state.

Co-Authored-By: Claude Opus 4.6 <[email protected]>

* fix: add anthropic-beta header required for OAuth authentication

Anthropic's api.anthropic.com requires the `anthropic-beta: oauth-2025-04-20`
header to accept OAuth Bearer tokens. Without it, the API returns 401
"OAuth authentication is currently not supported."

Also reverts API version to 2023-06-01 since the OAuth beta flag does
not support the 2024-10-22 version (returns 400 "not a valid version").

This was the same bug that caused PR #143's 401 errors — the beta header
was missing entirely.

Co-Authored-By: Claude Opus 4.6 <[email protected]>

* fix: Anthropic and OpenAI model resolution respects selected_model

The Anthropic and OpenAI config resolution ignored settings.selected_model
entirely, only checking the provider-specific env var (ANTHROPIC_MODEL,
OPENAI_MODEL) and falling back to a hardcoded default. This meant the
model chosen during onboarding wizard was silently overridden.

Now follows the same pattern as NearAI and OpenAI-compatible:
env var > settings.selected_model > hardcoded default.

Also deduplicated the Anthropic config construction (two identical
branches for API key vs OAuth now share model/base_url resolution).

Co-Authored-By: Claude Opus 4.6 <[email protected]>

* test: add provider resolution tests for all LLM backends

Covers deferred resolution (no credentials → None instead of error),
credential presence, model selection fallback chain, and OAuth token
routing for Anthropic, OpenAI, Tinfoil, Ollama, and NearAI.

Co-Authored-By: Claude Opus 4.6 <[email protected]>

* fix: handle nested tokens.access_token format in Codex auth.json

Codex CLI stores OAuth tokens in a nested format under
tokens.access_token (ChatGPT OAuth flow), not at the top level.
Also adds ENV_MUTEX to Codex token tests for thread safety.

Co-Authored-By: Claude Opus 4.6 <[email protected]>

* refactor: remove Codex OAuth onboarding (incompatible with OpenAI API)

Codex CLI OAuth tokens use a different endpoint
(chatgpt.com/backend-api/codex) and the Responses API wire format,
not api.openai.com with Chat Completions. The tokens lack the
model.request scope needed for the platform API, so they can't be
used as drop-in OPENAI_API_KEY replacements.

Removes: extract_codex_oauth_token(), wizard Codex OAuth flow,
CODEX_OAUTH_TOKEN env var support, and related tests.

OpenAI onboarding now uses direct API key only.

Co-Authored-By: Claude Opus 4.6 <[email protected]>

* style: fix formatting for CI (cargo fmt)

Co-Authored-By: Claude Opus 4.6 <[email protected]>

* fix: address Gemini review feedback

- Use ? operator for ANTHROPIC_MODEL/BASE_URL env resolution instead of
  .ok().flatten() to propagate ConfigErrors consistently
- Skip Tool messages without tool_call_id with a warning instead of
  using unwrap_or_default() which would send empty string to Anthropic
- Extract credential check into closure to reduce duplication in
  Claude Code sandbox setup

Co-Authored-By: Claude Opus 4.6 <[email protected]>

* refactor(review): address PR review feedback for OAuth onboarding

- Gate ANTHROPIC_OAUTH_TOKEN resolution to Anthropic provider only
  (was needlessly checked for all registry providers)
- Add 3 regression tests for OAuth config resolution:
  - oauth_token sets placeholder api_key
  - real api_key takes priority over oauth
  - non-Anthropic providers don't pick up oauth_token
- Validate OAuth token prefix (sk-ant-oat) in wizard to catch
  accidentally pasted API keys
- Improve error body read handling in AnthropicOAuthProvider
  (was silently swallowing read errors with unwrap_or_default)
- Remove extra blank line in write_bootstrap_env
- Remove stale blank line in RegistryProviderConfig doc comment

[skip-regression-check]

Co-Authored-By: Claude Opus 4.6 <[email protected]>

* fix: address PR #384 review comments

Blocker:
- Replace OnceLock<HashMap> with LazyLock<Mutex<HashMap>> for INJECTED_VARS
  so both inject_os_credentials() and inject_llm_keys_from_secrets() merge
  data instead of the second caller silently dropping its entries.

High:
- Add 401 retry with OS credential store re-extraction in
  AnthropicOAuthProvider, recovering from expired OAuth tokens (~8-12h)
  without manual intervention.
- Fix comment in app.rs: ~/.codex/auth.json → ~/.claude/.credentials.json.

Medium:
- Remove unsafe { std::env::set_var } from wizard; use thread-safe
  inject_single_var() overlay instead (safe on multi-threaded Tokio).
- Add post-init validation in AppBuilder: fail early with clear error when
  LLM_BACKEND is set but no credentials were resolved after secret injection.
- Add sk-ant-oat prefix validation in parse_oauth_access_token().
- Only route to AnthropicOAuthProvider when api_key is missing or equals
  OAUTH_PLACEHOLDER (API key takes priority over OAuth token).
- Teach fetch_anthropic_models() to use Bearer auth when only OAuth token
  is available (model listing no longer fails for OAuth-only users).

Low:
- Use optional_env() in wizard credential checks to read from injected
  overlay, not just raw env vars.

[skip-regression-check]

Co-Authored-By: Claude Opus 4.6 <[email protected]>

* style: cargo fmt

Co-Authored-By: Claude Opus 4.6 <[email protected]>

---------

Co-authored-by: Claude Opus 4.6 <[email protected]>
Co-authored-by: [email protected] <[email protected]>

.env.example

@@ -6,6 +6,18 @@ DATABASE_POOL_SIZE=10
 # LLM_BACKEND=nearai           # default
 # Possible values: nearai, ollama, openai_compatible, openai, anthropic, tinfoil
 
+# === Anthropic Direct ===
+# Two auth modes:
+#   1. API key: Set ANTHROPIC_API_KEY (from console.anthropic.com/settings/keys)
+#   2. OAuth token: Set ANTHROPIC_OAUTH_TOKEN (from `claude login`)
+#      OAuth tokens use Authorization: Bearer instead of x-api-key header.
+# ANTHROPIC_API_KEY=sk-ant-...
+# ANTHROPIC_OAUTH_TOKEN=sk-ant-oat01-...   # from `claude login` credentials
+# ANTHROPIC_MODEL=claude-sonnet-4-20250514
+
+# === OpenAI Direct ===
+# OPENAI_API_KEY=sk-...
+
 # === NEAR AI (Chat Completions API) ===
 # Two auth modes:
 #   1. Session token (default): Uses browser OAuth (GitHub/Google) on first run.

src/app.rs

@@ -244,11 +244,28 @@ impl AppBuilder {
         let master_key = match self.config.secrets.master_key() {
             Some(k) => k,
             None => {
+                // No secrets DB available, but we can still load tokens from
+                // OS credential stores (e.g., Anthropic OAuth via Claude Code's
+                // macOS Keychain / Linux ~/.claude/.credentials.json).
+                crate::config::inject_os_credentials();
+
                 // Consume unused handles
                 #[cfg(feature = "libsql")]
                 {
                     self.libsql_db.take();
                 }
+
+                // Re-resolve config with OS credentials
+                if let Some(ref db) = self.db {
+                    let toml_path = self.toml_path.as_deref();
+                    if let Ok(refreshed) =
+                        Config::from_db_with_toml(db.as_ref(), "default", toml_path).await
+                    {
+                        self.config = refreshed;
+                        tracing::debug!("LlmConfig re-resolved after OS credential injection");
+                    }
+                }
+
                 return Ok(());
             }
         };
@@ -665,6 +682,17 @@ impl AppBuilder {
         self.init_database().await?;
         self.init_secrets().await?;
 
+        // Post-init validation: if a non-nearai backend was selected but
+        // credentials were never resolved (deferred resolution found no keys),
+        // fail early with a clear error instead of a confusing runtime failure.
+        if self.config.llm.backend != "nearai" && self.config.llm.provider.is_none() {
+            let backend = &self.config.llm.backend;
+            anyhow::bail!(
+                "LLM_BACKEND={backend} is configured but no credentials were found. \
+                 Set the appropriate API key environment variable or run the setup wizard."
+            );
+        }
+
         let (llm, cheap_llm, recording_handle) = if let Some(llm) = self.llm_override.take() {
             (llm, None, None)
         } else {

src/config/helpers.rs

@@ -25,8 +25,13 @@ pub(crate) fn optional_env(key: &str) -> Result<Option<String>, ConfigError> {
     }
 
     // Fall back to thread-safe overlay (secrets injected from DB)
-    if let Some(val) = INJECTED_VARS.get().and_then(|map| map.get(key)) {
+    if let Some(val) = INJECTED_VARS
-        return Ok(Some(val.clone()));
+        .lock()
+        .unwrap_or_else(|p| p.into_inner())
+        .get(key)
+        .cloned()
+    {
+        return Ok(Some(val));
     }
 
     Ok(None)

src/config/llm.rs

@@ -9,6 +9,13 @@ use crate::llm::registry::{ProviderProtocol, ProviderRegistry};
 use crate::llm::session::SessionConfig;
 use crate::settings::Settings;
 
+/// Sentinel value used as `api_key` when only an OAuth token is present.
+///
+/// When we only have an OAuth token the provider factory in `llm/mod.rs`
+/// checks for this value and routes to `AnthropicOAuthProvider`, so this
+/// placeholder is never sent over the wire.
+pub const OAUTH_PLACEHOLDER: &str = "oauth-placeholder";
+
 /// Prompt cache retention policy for Anthropic.
 ///
 /// Controls Anthropic's automatic prompt caching via a top-level
@@ -66,6 +73,7 @@ pub struct RegistryProviderConfig {
     /// Provider identifier (e.g., "groq", "openai", "tinfoil").
     pub provider_id: String,
     /// API key (optional for some providers like Ollama).
+    /// For Anthropic OAuth, this is set to `OAUTH_PLACEHOLDER`.
     pub api_key: Option<SecretString>,
     /// Base URL for the API endpoint.
     pub base_url: String,
@@ -73,6 +81,9 @@ pub struct RegistryProviderConfig {
     pub model: String,
     /// Extra HTTP headers injected into every request.
     pub extra_headers: Vec<(String, String)>,
+    /// OAuth token for providers that support Bearer auth (e.g. Anthropic via `claude login`).
+    /// When set, the provider factory routes to the OAuth-specific provider implementation.
+    pub oauth_token: Option<SecretString>,
 }
 
 /// LLM provider configuration.
@@ -366,6 +377,22 @@ impl LlmConfig {
             Vec::new()
         };
 
+        // Resolve OAuth token (Anthropic-specific: `claude login` flow).
+        // Only check for OAuth token when the provider is actually Anthropic.
+        let oauth_token = if canonical_id == "anthropic" {
+            optional_env("ANTHROPIC_OAUTH_TOKEN")?.map(SecretString::from)
+        } else {
+            None
+        };
+        let api_key = if api_key.is_none() && oauth_token.is_some() {
+            // OAuth token present but no API key: use a placeholder so the
+            // config block is populated. The provider factory will route to
+            // the OAuth provider instead of rig-core's x-api-key client.
+            Some(SecretString::from(OAUTH_PLACEHOLDER.to_string()))
+        } else {
+            api_key
+        };
+
         Ok(RegistryProviderConfig {
             protocol,
             provider_id: canonical_id.to_string(),
@@ -373,6 +400,7 @@ impl LlmConfig {
             base_url,
             model,
             extra_headers,
+            oauth_token,
         })
     }
 }
@@ -677,8 +705,6 @@ mod tests {
 
     #[test]
     fn backend_alias_normalized_to_canonical_id() {
-        // When the user sets LLM_BACKEND to an alias (e.g., "open_ai"),
-        // LlmConfig.backend should resolve to the canonical ID ("openai").
         let _guard = ENV_MUTEX.lock().expect("env mutex poisoned");
         clear_openai_compatible_env();
         // SAFETY: Under ENV_MUTEX.
@@ -705,8 +731,6 @@ mod tests {
 
     #[test]
     fn unknown_backend_falls_back_to_openai_compatible() {
-        // An unrecognized LLM_BACKEND should fall back to the openai_compatible
-        // provider definition instead of erroring.
         let _guard = ENV_MUTEX.lock().expect("env mutex poisoned");
         clear_openai_compatible_env();
         // SAFETY: Under ENV_MUTEX.
@@ -717,7 +741,6 @@ mod tests {
 
         let settings = Settings::default();
         let cfg = LlmConfig::resolve(&settings).expect("resolve should succeed");
-        // Falls back to openai_compatible since "some_custom_provider" is unknown
         assert_eq!(cfg.backend, "openai_compatible");
         let provider = cfg.provider.expect("should have provider config");
         assert_eq!(provider.provider_id, "openai_compatible");
@@ -759,7 +782,6 @@ mod tests {
 
     #[test]
     fn base_url_resolution_priority() {
-        // Env var > settings > registry default
         let _guard = ENV_MUTEX.lock().expect("env mutex poisoned");
         clear_openai_compatible_env();
 
@@ -800,6 +822,119 @@ mod tests {
         }
     }
 
+    // ── OAuth resolution tests ──────────────────────────────────────
+
+    /// Clear all Anthropic-related env vars.
+    fn clear_anthropic_env() {
+        // SAFETY: Only called under ENV_MUTEX in tests.
+        unsafe {
+            std::env::remove_var("LLM_BACKEND");
+            std::env::remove_var("ANTHROPIC_API_KEY");
+            std::env::remove_var("ANTHROPIC_OAUTH_TOKEN");
+            std::env::remove_var("ANTHROPIC_MODEL");
+            std::env::remove_var("ANTHROPIC_BASE_URL");
+        }
+    }
+
+    #[test]
+    fn anthropic_oauth_token_sets_placeholder_api_key() {
+        use secrecy::ExposeSecret;
+
+        let _guard = ENV_MUTEX.lock().expect("env mutex poisoned");
+        clear_anthropic_env();
+        // SAFETY: Under ENV_MUTEX.
+        unsafe {
+            std::env::set_var("ANTHROPIC_OAUTH_TOKEN", "sk-ant-oat01-test-token");
+        }
+
+        let settings = Settings {
+            llm_backend: Some("anthropic".to_string()),
+            ..Default::default()
+        };
+        let cfg = LlmConfig::resolve(&settings).expect("resolve should succeed");
+        let provider = cfg.provider.expect("provider config should be present");
+
+        assert_eq!(
+            provider
+                .api_key
+                .as_ref()
+                .map(|k| k.expose_secret().to_string()),
+            Some(OAUTH_PLACEHOLDER.to_string()),
+            "api_key should be the OAuth placeholder when only OAuth token is set"
+        );
+        assert!(
+            provider.oauth_token.is_some(),
+            "oauth_token should be populated"
+        );
+        assert_eq!(
+            provider.oauth_token.as_ref().unwrap().expose_secret(),
+            "sk-ant-oat01-test-token"
+        );
+
+        clear_anthropic_env();
+    }
+
+    #[test]
+    fn anthropic_api_key_takes_priority_over_oauth() {
+        use secrecy::ExposeSecret;
+
+        let _guard = ENV_MUTEX.lock().expect("env mutex poisoned");
+        clear_anthropic_env();
+        // SAFETY: Under ENV_MUTEX.
+        unsafe {
+            std::env::set_var("ANTHROPIC_API_KEY", "sk-ant-real-key");
+            std::env::set_var("ANTHROPIC_OAUTH_TOKEN", "sk-ant-oat01-test-token");
+        }
+
+        let settings = Settings {
+            llm_backend: Some("anthropic".to_string()),
+            ..Default::default()
+        };
+        let cfg = LlmConfig::resolve(&settings).expect("resolve should succeed");
+        let provider = cfg.provider.expect("provider config should be present");
+
+        assert_eq!(
+            provider
+                .api_key
+                .as_ref()
+                .map(|k| k.expose_secret().to_string()),
+            Some("sk-ant-real-key".to_string()),
+            "real API key should take priority over OAuth placeholder"
+        );
+        assert!(
+            provider.oauth_token.is_some(),
+            "oauth_token should still be populated"
+        );
+
+        clear_anthropic_env();
+    }
+
+    #[test]
+    fn non_anthropic_provider_has_no_oauth_token() {
+        let _guard = ENV_MUTEX.lock().expect("env mutex poisoned");
+        clear_anthropic_env();
+        // SAFETY: Under ENV_MUTEX.
+        unsafe {
+            std::env::set_var("ANTHROPIC_OAUTH_TOKEN", "sk-ant-oat01-test-token");
+        }
+
+        let settings = Settings {
+            llm_backend: Some("openai".to_string()),
+            ..Default::default()
+        };
+        let cfg = LlmConfig::resolve(&settings).expect("resolve should succeed");
+        let provider = cfg.provider.expect("provider config should be present");
+
+        assert!(
+            provider.oauth_token.is_none(),
+            "non-Anthropic providers should not pick up ANTHROPIC_OAUTH_TOKEN"
+        );
+
+        clear_anthropic_env();
+    }
+
+    // ── Cache retention tests ───────────────────────────────────────
+
     #[test]
     fn cache_retention_from_str_primary_values() {
         assert_eq!(

src/config/mod.rs

@@ -13,7 +13,7 @@ mod embeddings;
 mod heartbeat;
 pub(crate) mod helpers;
 mod hygiene;
-mod llm;
+pub(crate) mod llm;
 mod routines;
 mod safety;
 mod sandbox;
@@ -24,7 +24,7 @@ mod tunnel;
 mod wasm;
 
 use std::collections::HashMap;
-use std::sync::OnceLock;
+use std::sync::{LazyLock, Mutex};
 
 use crate::error::ConfigError;
 use crate::settings::Settings;
@@ -53,7 +53,12 @@ pub use crate::llm::session::SessionConfig;
 /// Used by `inject_llm_keys_from_secrets()` to make API keys available to
 /// `optional_env()` without unsafe `set_var` calls. `optional_env()` checks
 /// real env vars first, then falls back to this overlay.
-static INJECTED_VARS: OnceLock<HashMap<String, String>> = OnceLock::new();
+///
+/// Uses `Mutex<HashMap>` instead of `OnceLock` so that both
+/// `inject_os_credentials()` and `inject_llm_keys_from_secrets()` can merge
+/// their data. Whichever runs first initialises the map; the second merges in.
+static INJECTED_VARS: LazyLock<Mutex<HashMap<String, String>>> =
+    LazyLock::new(|| Mutex::new(HashMap::new()));
 
 /// Main configuration for the agent.
 #[derive(Debug, Clone)]
@@ -285,6 +290,9 @@ impl Config {
 /// env-var-first resolution in `LlmConfig::resolve()`. Keys in the overlay
 /// are read by `optional_env()` before falling back to `std::env::var()`,
 /// so explicit env vars always win.
+///
+/// Also loads tokens from OS credential stores (macOS Keychain, Linux
+/// credentials files) which don't require the secrets DB.
 pub async fn inject_llm_keys_from_secrets(
     secrets: &dyn crate::secrets::SecretsStore,
     user_id: &str,
@@ -292,7 +300,10 @@ pub async fn inject_llm_keys_from_secrets(
     // Static mappings for well-known providers.
     // The registry's setup hints define secret_name -> env_var mappings,
     // so new providers added to providers.json get injection automatically.
-    let mut mappings: Vec<(&str, &str)> = vec![("llm_nearai_api_key", "NEARAI_API_KEY")];
+    let mut mappings: Vec<(&str, &str)> = vec![
+        ("llm_nearai_api_key", "NEARAI_API_KEY"),
+        ("llm_anthropic_oauth_token", "ANTHROPIC_OAUTH_TOKEN"),
+    ];
 
     // Dynamically discover secret->env mappings from the provider registry.
     // Uses selectable() which deduplicates user overrides correctly.
@@ -331,5 +342,62 @@ pub async fn inject_llm_keys_from_secrets(
         }
     }
 
-    let _ = INJECTED_VARS.set(injected);
+    inject_os_credential_store_tokens(&mut injected);
+
+    merge_injected_vars(injected);
+}
+
+/// Load tokens from OS credential stores (no DB required).
+///
+/// Called unconditionally during startup — even when the encrypted secrets DB
+/// is unavailable (no master key, no DB connection). This ensures OAuth tokens
+/// from `claude login` (macOS Keychain / Linux credentials.json)
+/// are available for config resolution.
+pub fn inject_os_credentials() {
+    let mut injected = HashMap::new();
+    inject_os_credential_store_tokens(&mut injected);
+    merge_injected_vars(injected);
+}
+
+/// Merge new entries into the global injected-vars overlay.
+///
+/// New keys are inserted; existing keys are overwritten (later callers win,
+/// e.g. fresh OS credential store tokens override stale DB copies).
+fn merge_injected_vars(new_entries: HashMap<String, String>) {
+    if new_entries.is_empty() {
+        return;
+    }
+    match INJECTED_VARS.lock() {
+        Ok(mut map) => map.extend(new_entries),
+        Err(poisoned) => poisoned.into_inner().extend(new_entries),
+    }
+}
+
+/// Inject a single key-value pair into the overlay.
+///
+/// Used by the setup wizard to make credentials available to `optional_env()`
+/// without calling `unsafe { std::env::set_var }`.
+pub fn inject_single_var(key: &str, value: &str) {
+    match INJECTED_VARS.lock() {
+        Ok(mut map) => {
+            map.insert(key.to_string(), value.to_string());
+        }
+        Err(poisoned) => {
+            poisoned
+                .into_inner()
+                .insert(key.to_string(), value.to_string());
+        }
+    }
+}
+
+/// Shared helper: extract tokens from OS credential stores into the overlay map.
+fn inject_os_credential_store_tokens(injected: &mut HashMap<String, String>) {
+    // Try the OS credential store for a fresh Anthropic OAuth token.
+    // Tokens from `claude login` expire in 8-12h, so the DB copy may be stale.
+    // A fresh extraction from macOS Keychain / Linux credentials.json wins
+    // over the (possibly expired) copy stored in the encrypted secrets DB.
+    if let Some(fresh) = crate::config::ClaudeCodeConfig::extract_oauth_token() {
+        injected.insert("ANTHROPIC_OAUTH_TOKEN".to_string(), fresh);
+        tracing::debug!("Refreshed ANTHROPIC_OAUTH_TOKEN from OS credential store");
+    }
 }

src/config/sandbox.rs

@@ -233,9 +233,14 @@ impl ClaudeCodeConfig {
 /// Expected shape: `{"claudeAiOauth": {"accessToken": "sk-ant-oat01-..."}}`
 fn parse_oauth_access_token(json: &str) -> Option<String> {
     let creds: serde_json::Value = serde_json::from_str(json).ok()?;
-    creds["claudeAiOauth"]["accessToken"]
+    let token = creds["claudeAiOauth"]["accessToken"].as_str()?;
-        .as_str()
+    // Validate that the token looks like a real OAuth token before using it.
-        .map(String::from)
+    // Claude CLI tokens start with "sk-ant-oat".
+    if !token.starts_with("sk-ant-oat") {
+        tracing::debug!("Ignoring credential store token with unexpected prefix");
+        return None;
+    }
+    Some(token.to_string())
 }
 
 #[cfg(test)]
@@ -401,14 +406,14 @@ mod tests {
     fn parse_oauth_token_nested_extra_fields() {
         let json = r#"{
             "claudeAiOauth": {
-                "accessToken": "sk-ant-real-token",
+                "accessToken": "sk-ant-oat01-real-token",
                 "refreshToken": "rt-abc",
                 "expiresAt": 1700000000
             }
         }"#;
         assert_eq!(
             parse_oauth_access_token(json),
-            Some("sk-ant-real-token".to_string())
+            Some("sk-ant-oat01-real-token".to_string())
         );
     }
 
@@ -418,6 +423,12 @@ mod tests {
         assert_eq!(parse_oauth_access_token(json), None);
     }
 
+    #[test]
+    fn parse_oauth_token_rejects_invalid_prefix() {
+        let json = r#"{"claudeAiOauth": {"accessToken": "not-an-oauth-token"}}"#;
+        assert_eq!(parse_oauth_access_token(json), None);
+    }
+
     // ── default_claude_code_allowed_tools ───────────────────────────
 
     #[test]

src/llm/anthropic_oauth.rs

@@ -0,0 +1,641 @@
+//! Anthropic OAuth provider (direct HTTP, `Authorization: Bearer`).
+//!
+//! This provider exists because the `rig-core` Anthropic client hardcodes the
+//! `x-api-key` header, which is rejected by Anthropic's OAuth tokens from
+//! `claude login`. OAuth tokens require `Authorization: Bearer <token>` instead.
+//!
+//! Pattern follows `nearai_chat.rs`: direct HTTP calls via `reqwest::Client`.
+
+use async_trait::async_trait;
+use reqwest::Client;
+use rust_decimal::Decimal;
+use secrecy::{ExposeSecret, SecretString};
+use serde::{Deserialize, Serialize};
+
+use crate::config::RegistryProviderConfig;
+use crate::error::LlmError;
+use crate::llm::costs;
+use crate::llm::provider::{
+    ChatMessage, CompletionRequest, CompletionResponse, FinishReason, LlmProvider, Role, ToolCall,
+    ToolCompletionRequest, ToolCompletionResponse,
+};
+
+const ANTHROPIC_API_URL: &str = "https://api.anthropic.com/v1/messages";
+/// OAuth beta requires 2023-06-01; the 2024-10-22 version is not valid with the beta flag.
+const ANTHROPIC_API_VERSION: &str = "2023-06-01";
+/// Required beta flag to enable OAuth Bearer auth on api.anthropic.com.
+/// Without this header, the API returns 401 "OAuth authentication is currently not supported."
+const ANTHROPIC_OAUTH_BETA: &str = "oauth-2025-04-20";
+const DEFAULT_MAX_TOKENS: u32 = 8192;
+
+/// Anthropic provider using OAuth Bearer authentication.
+pub struct AnthropicOAuthProvider {
+    client: Client,
+    token: SecretString,
+    model: String,
+    base_url: Option<String>,
+    active_model: std::sync::RwLock<String>,
+}
+
+impl AnthropicOAuthProvider {
+    pub fn new(config: &RegistryProviderConfig) -> Result<Self, LlmError> {
+        let token = config
+            .oauth_token
+            .clone()
+            .ok_or_else(|| LlmError::AuthFailed {
+                provider: "anthropic_oauth".to_string(),
+            })?;
+
+        let client = Client::builder()
+            .timeout(std::time::Duration::from_secs(120))
+            .build()
+            .map_err(|e| LlmError::RequestFailed {
+                provider: "anthropic_oauth".to_string(),
+                reason: format!("Failed to build HTTP client: {}", e),
+            })?;
+
+        let active_model = std::sync::RwLock::new(config.model.clone());
+        let base_url = if config.base_url.is_empty() {
+            None
+        } else {
+            Some(config.base_url.clone())
+        };
+
+        Ok(Self {
+            client,
+            token,
+            model: config.model.clone(),
+            base_url,
+            active_model,
+        })
+    }
+
+    fn api_url(&self) -> String {
+        if let Some(ref base) = self.base_url {
+            let base = base.trim_end_matches('/');
+            format!("{}/v1/messages", base)
+        } else {
+            ANTHROPIC_API_URL.to_string()
+        }
+    }
+
+    async fn send_request<R: for<'de> Deserialize<'de>>(
+        &self,
+        body: &AnthropicRequest,
+    ) -> Result<R, LlmError> {
+        let url = self.api_url();
+
+        tracing::debug!("Sending request to Anthropic OAuth: {}", url);
+
+        let response = self
+            .client
+            .post(&url)
+            .bearer_auth(self.token.expose_secret())
+            .header("anthropic-version", ANTHROPIC_API_VERSION)
+            .header("anthropic-beta", ANTHROPIC_OAUTH_BETA)
+            .header("Content-Type", "application/json")
+            .json(body)
+            .send()
+            .await
+            .map_err(|e| LlmError::RequestFailed {
+                provider: "anthropic_oauth".to_string(),
+                reason: e.to_string(),
+            })?;
+
+        let status = response.status();
+
+        if !status.is_success() {
+            // Parse Retry-After header before consuming the body.
+            let retry_after = response
+                .headers()
+                .get("retry-after")
+                .and_then(|v| v.to_str().ok())
+                .and_then(|v| v.parse::<u64>().ok())
+                .map(std::time::Duration::from_secs);
+
+            let response_text = response
+                .text()
+                .await
+                .unwrap_or_else(|e| format!("(failed to read error body: {e})"));
+
+            if status.as_u16() == 401 {
+                // OAuth tokens from `claude login` expire in ~8-12h. Attempt
+                // to re-extract a fresh token from the OS credential store
+                // (macOS Keychain / Linux credentials file) before giving up.
+                if let Some(fresh) = crate::config::ClaudeCodeConfig::extract_oauth_token() {
+                    let fresh_token = SecretString::from(fresh);
+                    // Retry once with the refreshed token
+                    let retry = self
+                        .client
+                        .post(&url)
+                        .bearer_auth(fresh_token.expose_secret())
+                        .header("anthropic-version", ANTHROPIC_API_VERSION)
+                        .header("anthropic-beta", ANTHROPIC_OAUTH_BETA)
+                        .header("Content-Type", "application/json")
+                        .json(body)
+                        .send()
+                        .await
+                        .map_err(|e| LlmError::RequestFailed {
+                            provider: "anthropic_oauth".to_string(),
+                            reason: e.to_string(),
+                        })?;
+                    if retry.status().is_success() {
+                        let text = retry.text().await.map_err(|e| LlmError::RequestFailed {
+                            provider: "anthropic_oauth".to_string(),
+                            reason: format!("Failed to read response body: {}", e),
+                        })?;
+                        return serde_json::from_str(&text).map_err(|e| {
+                            let truncated = crate::agent::truncate_for_preview(&text, 512);
+                            LlmError::InvalidResponse {
+                                provider: "anthropic_oauth".to_string(),
+                                reason: format!("JSON parse error: {}. Raw: {}", e, truncated),
+                            }
+                        });
+                    }
+                    tracing::warn!(
+                        "Anthropic OAuth 401 retry with refreshed token also failed ({})",
+                        retry.status()
+                    );
+                }
+                return Err(LlmError::AuthFailed {
+                    provider: "anthropic_oauth".to_string(),
+                });
+            }
+            if status.as_u16() == 429 {
+                return Err(LlmError::RateLimited {
+                    provider: "anthropic_oauth".to_string(),
+                    retry_after,
+                });
+            }
+            let truncated = crate::agent::truncate_for_preview(&response_text, 512);
+            return Err(LlmError::RequestFailed {
+                provider: "anthropic_oauth".to_string(),
+                reason: format!("HTTP {}: {}", status, truncated),
+            });
+        }
+
+        let response_text = response.text().await.map_err(|e| LlmError::RequestFailed {
+            provider: "anthropic_oauth".to_string(),
+            reason: format!("Failed to read response body: {}", e),
+        })?;
+
+        tracing::debug!(
+            "Anthropic OAuth response: status={}, bytes={}",
+            status,
+            response_text.len()
+        );
+
+        serde_json::from_str(&response_text).map_err(|e| {
+            let truncated = crate::agent::truncate_for_preview(&response_text, 512);
+            LlmError::InvalidResponse {
+                provider: "anthropic_oauth".to_string(),
+                reason: format!("JSON parse error: {}. Raw: {}", e, truncated),
+            }
+        })
+    }
+}
+
+#[async_trait]
+impl LlmProvider for AnthropicOAuthProvider {
+    async fn complete(&self, req: CompletionRequest) -> Result<CompletionResponse, LlmError> {
+        let model = req.model.unwrap_or_else(|| self.active_model_name());
+        let (system, messages) = convert_messages(req.messages);
+
+        let request = AnthropicRequest {
+            model,
+            messages,
+            system,
+            max_tokens: req.max_tokens.unwrap_or(DEFAULT_MAX_TOKENS),
+            temperature: req.temperature,
+            tools: None,
+            tool_choice: None,
+        };
+
+        let response: AnthropicResponse = self.send_request(&request).await?;
+        let (content, _tool_calls) = extract_response_content(&response);
+
+        let finish_reason = match response.stop_reason.as_deref() {
+            Some("end_turn") | Some("stop") => FinishReason::Stop,
+            Some("max_tokens") => FinishReason::Length,
+            Some("tool_use") => FinishReason::ToolUse,
+            _ => FinishReason::Unknown,
+        };
+
+        Ok(CompletionResponse {
+            content: content.unwrap_or_default(),
+            finish_reason,
+            input_tokens: response.usage.input_tokens,
+            output_tokens: response.usage.output_tokens,
+            cache_creation_input_tokens: response.usage.cache_creation_input_tokens,
+            cache_read_input_tokens: response.usage.cache_read_input_tokens,
+        })
+    }
+
+    async fn complete_with_tools(
+        &self,
+        req: ToolCompletionRequest,
+    ) -> Result<ToolCompletionResponse, LlmError> {
+        let model = req.model.unwrap_or_else(|| self.active_model_name());
+        let (system, messages) = convert_messages(req.messages);
+
+        let tools: Vec<AnthropicTool> = req
+            .tools
+            .into_iter()
+            .map(|t| AnthropicTool {
+                name: t.name,
+                description: t.description,
+                input_schema: t.parameters,
+            })
+            .collect();
+
+        // Map tool_choice from OpenAI format to Anthropic format
+        let tool_choice = req.tool_choice.map(|tc| match tc.as_str() {
+            "auto" => AnthropicToolChoice {
+                choice_type: "auto".to_string(),
+                name: None,
+            },
+            "required" => AnthropicToolChoice {
+                choice_type: "any".to_string(),
+                name: None,
+            },
+            "none" => AnthropicToolChoice {
+                choice_type: "none".to_string(),
+                name: None,
+            },
+            specific => AnthropicToolChoice {
+                choice_type: "tool".to_string(),
+                name: Some(specific.to_string()),
+            },
+        });
+
+        let request = AnthropicRequest {
+            model,
+            messages,
+            system,
+            max_tokens: req.max_tokens.unwrap_or(DEFAULT_MAX_TOKENS),
+            temperature: req.temperature,
+            tools: if tools.is_empty() { None } else { Some(tools) },
+            tool_choice,
+        };
+
+        let response: AnthropicResponse = self.send_request(&request).await?;
+        let (content, tool_calls) = extract_response_content(&response);
+
+        let finish_reason = match response.stop_reason.as_deref() {
+            Some("end_turn") | Some("stop") => FinishReason::Stop,
+            Some("max_tokens") => FinishReason::Length,
+            Some("tool_use") => FinishReason::ToolUse,
+            _ => {
+                if !tool_calls.is_empty() {
+                    FinishReason::ToolUse
+                } else {
+                    FinishReason::Unknown
+                }
+            }
+        };
+
+        Ok(ToolCompletionResponse {
+            content,
+            tool_calls,
+            finish_reason,
+            input_tokens: response.usage.input_tokens,
+            output_tokens: response.usage.output_tokens,
+            cache_creation_input_tokens: response.usage.cache_creation_input_tokens,
+            cache_read_input_tokens: response.usage.cache_read_input_tokens,
+        })
+    }
+
+    fn model_name(&self) -> &str {
+        &self.model
+    }
+
+    fn cost_per_token(&self) -> (Decimal, Decimal) {
+        let model = self.active_model_name();
+        costs::model_cost(&model).unwrap_or_else(costs::default_cost)
+    }
+
+    fn active_model_name(&self) -> String {
+        match self.active_model.read() {
+            Ok(guard) => guard.clone(),
+            Err(poisoned) => poisoned.into_inner().clone(),
+        }
+    }
+
+    fn set_model(&self, model: &str) -> Result<(), LlmError> {
+        match self.active_model.write() {
+            Ok(mut guard) => {
+                *guard = model.to_string();
+            }
+            Err(poisoned) => {
+                *poisoned.into_inner() = model.to_string();
+            }
+        }
+        Ok(())
+    }
+}
+
+// --- Anthropic Messages API types ---
+
+#[derive(Debug, Serialize)]
+struct AnthropicRequest {
+    model: String,
+    messages: Vec<AnthropicMessage>,
+    #[serde(skip_serializing_if = "Option::is_none")]
+    system: Option<String>,
+    max_tokens: u32,
+    #[serde(skip_serializing_if = "Option::is_none")]
+    temperature: Option<f32>,
+    #[serde(skip_serializing_if = "Option::is_none")]
+    tools: Option<Vec<AnthropicTool>>,
+    #[serde(skip_serializing_if = "Option::is_none")]
+    tool_choice: Option<AnthropicToolChoice>,
+}
+
+#[derive(Debug, Serialize)]
+struct AnthropicMessage {
+    role: String,
+    content: AnthropicContent,
+}
+
+/// Anthropic content can be a simple string or a list of content blocks.
+#[derive(Debug, Serialize)]
+#[serde(untagged)]
+enum AnthropicContent {
+    Text(String),
+    Blocks(Vec<AnthropicContentBlock>),
+}
+
+#[derive(Debug, Serialize)]
+#[serde(tag = "type")]
+enum AnthropicContentBlock {
+    #[serde(rename = "text")]
+    Text { text: String },
+    #[serde(rename = "tool_use")]
+    ToolUse {
+        id: String,
+        name: String,
+        input: serde_json::Value,
+    },
+    #[serde(rename = "tool_result")]
+    ToolResult {
+        tool_use_id: String,
+        content: String,
+    },
+}
+
+#[derive(Debug, Serialize)]
+struct AnthropicTool {
+    name: String,
+    description: String,
+    input_schema: serde_json::Value,
+}
+
+#[derive(Debug, Serialize)]
+struct AnthropicToolChoice {
+    #[serde(rename = "type")]
+    choice_type: String,
+    #[serde(skip_serializing_if = "Option::is_none")]
+    name: Option<String>,
+}
+
+#[derive(Debug, Deserialize)]
+struct AnthropicResponse {
+    content: Vec<AnthropicResponseBlock>,
+    #[serde(default)]
+    stop_reason: Option<String>,
+    usage: AnthropicUsage,
+}
+
+#[derive(Debug, Deserialize)]
+#[serde(tag = "type")]
+enum AnthropicResponseBlock {
+    #[serde(rename = "text")]
+    Text { text: String },
+    #[serde(rename = "tool_use")]
+    ToolUse {
+        id: String,
+        name: String,
+        input: serde_json::Value,
+    },
+}
+
+#[derive(Debug, Deserialize)]
+struct AnthropicUsage {
+    #[serde(default)]
+    input_tokens: u32,
+    #[serde(default)]
+    output_tokens: u32,
+    #[serde(default)]
+    cache_creation_input_tokens: u32,
+    #[serde(default)]
+    cache_read_input_tokens: u32,
+}
+
+/// Convert ChatMessage list to Anthropic format.
+///
+/// Extracts system messages to the top-level `system` parameter (Anthropic
+/// doesn't allow system messages in the `messages` array). Tool-call/tool-result
+/// pairs are converted to content blocks.
+fn convert_messages(messages: Vec<ChatMessage>) -> (Option<String>, Vec<AnthropicMessage>) {
+    let mut system_parts: Vec<String> = Vec::new();
+    let mut anthropic_msgs: Vec<AnthropicMessage> = Vec::new();
+
+    for msg in messages {
+        match msg.role {
+            Role::System => {
+                if !msg.content.is_empty() {
+                    system_parts.push(msg.content);
+                }
+            }
+            Role::User => {
+                anthropic_msgs.push(AnthropicMessage {
+                    role: "user".to_string(),
+                    content: AnthropicContent::Text(msg.content),
+                });
+            }
+            Role::Assistant => {
+                if let Some(tool_calls) = msg.tool_calls {
+                    // Assistant message with tool calls → content blocks
+                    let mut blocks: Vec<AnthropicContentBlock> = Vec::new();
+                    if !msg.content.is_empty() {
+                        blocks.push(AnthropicContentBlock::Text { text: msg.content });
+                    }
+                    for tc in tool_calls {
+                        blocks.push(AnthropicContentBlock::ToolUse {
+                            id: tc.id,
+                            name: tc.name,
+                            input: tc.arguments,
+                        });
+                    }
+                    anthropic_msgs.push(AnthropicMessage {
+                        role: "assistant".to_string(),
+                        content: AnthropicContent::Blocks(blocks),
+                    });
+                } else {
+                    anthropic_msgs.push(AnthropicMessage {
+                        role: "assistant".to_string(),
+                        content: AnthropicContent::Text(msg.content),
+                    });
+                }
+            }
+            Role::Tool => {
+                let Some(tool_call_id) = msg.tool_call_id else {
+                    tracing::warn!("Skipping Tool message without tool_call_id");
+                    continue;
+                };
+                // Tool results go into a user message with tool_result blocks
+                let block = AnthropicContentBlock::ToolResult {
+                    tool_use_id: tool_call_id,
+                    content: msg.content,
+                };
+                // If the last message is already a user message with blocks,
+                // append to it (Anthropic requires consecutive tool results
+                // in one user message).
+                if let Some(last) = anthropic_msgs.last_mut()
+                    && last.role == "user"
+                    && let AnthropicContent::Blocks(ref mut blocks) = last.content
+                {
+                    blocks.push(block);
+                    continue;
+                }
+                anthropic_msgs.push(AnthropicMessage {
+                    role: "user".to_string(),
+                    content: AnthropicContent::Blocks(vec![block]),
+                });
+            }
+        }
+    }
+
+    let system = if system_parts.is_empty() {
+        None
+    } else {
+        Some(system_parts.join("\n\n"))
+    };
+
+    (system, anthropic_msgs)
+}
+
+/// Extract text content and tool calls from an Anthropic response.
+fn extract_response_content(response: &AnthropicResponse) -> (Option<String>, Vec<ToolCall>) {
+    let mut text_parts: Vec<String> = Vec::new();
+    let mut tool_calls: Vec<ToolCall> = Vec::new();
+
+    for block in &response.content {
+        match block {
+            AnthropicResponseBlock::Text { text } => {
+                text_parts.push(text.clone());
+            }
+            AnthropicResponseBlock::ToolUse { id, name, input } => {
+                tool_calls.push(ToolCall {
+                    id: id.clone(),
+                    name: name.clone(),
+                    arguments: input.clone(),
+                });
+            }
+        }
+    }
+
+    let content = if text_parts.is_empty() {
+        None
+    } else {
+        Some(text_parts.join(""))
+    };
+
+    (content, tool_calls)
+}
+
+#[cfg(test)]
+mod tests {
+    use super::*;
+
+    #[test]
+    fn test_convert_messages_extracts_system() {
+        let messages = vec![
+            ChatMessage::system("You are helpful."),
+            ChatMessage::user("Hello"),
+        ];
+        let (system, msgs) = convert_messages(messages);
+        assert_eq!(system, Some("You are helpful.".to_string()));
+        assert_eq!(msgs.len(), 1);
+        assert_eq!(msgs[0].role, "user");
+    }
+
+    #[test]
+    fn test_convert_messages_multiple_systems() {
+        let messages = vec![
+            ChatMessage::system("System 1"),
+            ChatMessage::system("System 2"),
+            ChatMessage::user("Hello"),
+        ];
+        let (system, msgs) = convert_messages(messages);
+        assert_eq!(system, Some("System 1\n\nSystem 2".to_string()));
+        assert_eq!(msgs.len(), 1);
+    }
+
+    #[test]
+    fn test_convert_messages_tool_calls() {
+        let tool_calls = vec![ToolCall {
+            id: "call_1".to_string(),
+            name: "search".to_string(),
+            arguments: serde_json::json!({"q": "test"}),
+        }];
+        let messages = vec![
+            ChatMessage::user("Search for test"),
+            ChatMessage::assistant_with_tool_calls(Some("Let me search.".to_string()), tool_calls),
+            ChatMessage::tool_result("call_1", "search", "found it"),
+        ];
+        let (system, msgs) = convert_messages(messages);
+        assert!(system.is_none());
+        assert_eq!(msgs.len(), 3);
+        assert_eq!(msgs[0].role, "user");
+        assert_eq!(msgs[1].role, "assistant");
+        // Tool result should be a user message
+        assert_eq!(msgs[2].role, "user");
+    }
+
+    #[test]
+    fn test_extract_response_text_only() {
+        let response = AnthropicResponse {
+            content: vec![AnthropicResponseBlock::Text {
+                text: "Hello!".to_string(),
+            }],
+            stop_reason: Some("end_turn".to_string()),
+            usage: AnthropicUsage {
+                input_tokens: 10,
+                output_tokens: 5,
+                cache_creation_input_tokens: 0,
+                cache_read_input_tokens: 0,
+            },
+        };
+        let (content, tool_calls) = extract_response_content(&response);
+        assert_eq!(content, Some("Hello!".to_string()));
+        assert!(tool_calls.is_empty());
+    }
+
+    #[test]
+    fn test_extract_response_with_tool_use() {
+        let response = AnthropicResponse {
+            content: vec![
+                AnthropicResponseBlock::Text {
+                    text: "Let me search.".to_string(),
+                },
+                AnthropicResponseBlock::ToolUse {
+                    id: "call_1".to_string(),
+                    name: "search".to_string(),
+                    input: serde_json::json!({"q": "test"}),
+                },
+            ],
+            stop_reason: Some("tool_use".to_string()),
+            usage: AnthropicUsage {
+                input_tokens: 20,
+                output_tokens: 15,
+                cache_creation_input_tokens: 0,
+                cache_read_input_tokens: 0,
+            },
+        };
+        let (content, tool_calls) = extract_response_content(&response);
+        assert_eq!(content, Some("Let me search.".to_string()));
+        assert_eq!(tool_calls.len(), 1);
+        assert_eq!(tool_calls[0].name, "search");
+    }
+}

src/llm/mod.rs

@@ -7,6 +7,7 @@
 //! - **Ollama**: Local model inference
 //! - **OpenAI-compatible**: Any endpoint that speaks the OpenAI API
 
+mod anthropic_oauth;
 pub mod circuit_breaker;
 pub mod costs;
 pub mod failover;
@@ -178,6 +179,24 @@ fn create_openai_compat_from_registry(
 fn create_anthropic_from_registry(
     config: &RegistryProviderConfig,
 ) -> Result<Arc<dyn LlmProvider>, LlmError> {
+    // Route to OAuth provider when an OAuth token is present and no real API
+    // key was provided. When both are set, the API key takes priority (standard
+    // x-api-key auth via rig-core).
+    let api_key_is_placeholder = config
+        .api_key
+        .as_ref()
+        .is_some_and(|k| k.expose_secret() == crate::config::llm::OAUTH_PLACEHOLDER);
+    if config.oauth_token.is_some() && (config.api_key.is_none() || api_key_is_placeholder) {
+        tracing::info!(
+            provider = %config.provider_id,
+            model = %config.model,
+            base_url = if config.base_url.is_empty() { "default" } else { &config.base_url },
+            "Using Anthropic OAuth API"
+        );
+        let provider = anthropic_oauth::AnthropicOAuthProvider::new(config)?;
+        return Ok(Arc::new(provider));
+    }
+
     use crate::config::CacheRetention;
     use crate::config::helpers::optional_env;
     use rig::providers::anthropic;

src/main.rs

@@ -158,7 +158,10 @@ async fn async_main() -> anyhow::Result<()> {
         wizard.run().await?;
     }
 
-    // Load initial config from env + disk + optional TOML (before DB is available)
+    // Load initial config from env + disk + optional TOML (before DB is available).
+    // Credentials may be missing at this point — that's fine. LlmConfig::resolve()
+    // defers gracefully, and AppBuilder::build_all() re-resolves after loading
+    // secrets from the encrypted DB.
     let toml_path = cli.config.as_deref();
     let config = match Config::from_env_with_toml(toml_path).await {
         Ok(c) => c,

src/settings.rs

@@ -498,6 +498,10 @@ pub struct SandboxSettings {
     /// Additional domains to allow through the network proxy.
     #[serde(default)]
     pub extra_allowed_domains: Vec<String>,
+
+    /// Whether Claude Code sandbox mode is enabled.
+    #[serde(default)]
+    pub claude_code_enabled: bool,
 }
 
 fn default_sandbox_policy() -> String {
@@ -531,6 +535,7 @@ impl Default for SandboxSettings {
             image: default_sandbox_image(),
             auto_pull_image: true,
             extra_allowed_domains: Vec::new(),
+            claude_code_enabled: false,
         }
     }
 }

src/setup/wizard.rs

@@ -22,6 +22,7 @@ use crate::bootstrap::ironclaw_base_dir;
 use crate::channels::wasm::{
     ChannelCapabilitiesFile, available_channel_names, install_bundled_channel,
 };
+use crate::config::llm::OAUTH_PLACEHOLDER;
 use crate::llm::{SessionConfig, SessionManager};
 use crate::secrets::{SecretsCrypto, SecretsStore};
 use crate::settings::{KeySource, Settings};
@@ -886,6 +887,11 @@ impl SetupWizard {
             return Ok(());
         };
 
+        // Anthropic has a custom flow: API key or OAuth token from `claude login`.
+        if provider_id == "anthropic" {
+            return self.setup_anthropic().await;
+        }
+
         match setup {
             crate::llm::registry::SetupHint::ApiKey {
                 secret_name,
@@ -991,6 +997,112 @@ impl SetupWizard {
         Ok(())
     }
 
+    /// Anthropic provider setup: API key or OAuth token from `claude login`.
+    async fn setup_anthropic(&mut self) -> Result<(), SetupError> {
+        let options = &["Direct API Key", "OAuth Token (from `claude login`)"];
+        let choice = select_one("How do you want to authenticate with Anthropic?", options)
+            .map_err(SetupError::Io)?;
+
+        if choice == 0 {
+            // Standard API key flow
+            self.setup_api_key_provider(
+                "anthropic",
+                "ANTHROPIC_API_KEY",
+                "llm_anthropic_api_key",
+                "Anthropic API key",
+                "https://console.anthropic.com/settings/keys",
+                None,
+            )
+            .await
+        } else {
+            // OAuth token flow
+            self.setup_anthropic_oauth().await
+        }
+    }
+
+    /// Anthropic OAuth setup: extract token from `claude login` credentials.
+    async fn setup_anthropic_oauth(&mut self) -> Result<(), SetupError> {
+        self.settings.llm_backend = Some("anthropic".to_string());
+        if self.settings.selected_model.is_some() {
+            self.settings.selected_model = None;
+        }
+
+        // Try to extract existing OAuth token from Claude Code credentials
+        if let Some(token) = crate::config::ClaudeCodeConfig::extract_oauth_token() {
+            print_info(&format!("Found OAuth token: {}", mask_api_key(&token)));
+            if confirm("Use this token?", true).map_err(SetupError::Io)? {
+                return self.save_anthropic_oauth_token(&token).await;
+            }
+        } else {
+            print_info("No OAuth token found from `claude login`.");
+            print_info("Run `claude login` in a terminal to authenticate, then retry.");
+            println!();
+
+            if confirm("Retry after running `claude login`?", true).map_err(SetupError::Io)? {
+                // Block until the user has run `claude login` in another terminal
+                input("Press Enter after running `claude login` in another terminal...")
+                    .map_err(SetupError::Io)?;
+                if let Some(token) = crate::config::ClaudeCodeConfig::extract_oauth_token() {
+                    print_info(&format!("Found OAuth token: {}", mask_api_key(&token)));
+                    return self.save_anthropic_oauth_token(&token).await;
+                }
+                print_error("Still no OAuth token found.");
+            }
+        }
+
+        // Fallback: let user paste the token manually, or switch to API key
+        print_info("You can paste your OAuth token directly (starts with sk-ant-oat01-).");
+        print_info("Or press Enter with no input to switch to the API key flow.");
+        let token = secret_input("Anthropic OAuth token").map_err(SetupError::Io)?;
+        let token_str = token.expose_secret();
+        if token_str.is_empty() {
+            print_info("Switching to API key flow...");
+            return self
+                .setup_api_key_provider(
+                    "anthropic",
+                    "ANTHROPIC_API_KEY",
+                    "llm_anthropic_api_key",
+                    "Anthropic API key",
+                    "https://console.anthropic.com/settings/keys",
+                    None,
+                )
+                .await;
+        }
+        self.save_anthropic_oauth_token(token_str).await
+    }
+
+    /// Save an Anthropic OAuth token to secrets and set env for immediate use.
+    async fn save_anthropic_oauth_token(&mut self, token: &str) -> Result<(), SetupError> {
+        // Validate token format to catch accidentally pasted API keys
+        if !token.starts_with("sk-ant-oat") {
+            print_error("Token doesn't look like an OAuth token (expected prefix: sk-ant-oat).");
+            print_info("If you have an API key instead, use the 'Direct API Key' option.");
+            return Err(SetupError::Config("Invalid OAuth token format".to_string()));
+        }
+
+        // Store in secrets if available
+        if let Ok(ctx) = self.init_secrets_context().await {
+            let key = SecretString::from(token.to_string());
+            ctx.save_secret("llm_anthropic_oauth_token", &key)
+                .await
+                .map_err(|e| SetupError::Config(format!("Failed to save OAuth token: {e}")))?;
+            print_success("OAuth token encrypted and saved");
+        } else {
+            print_info("Secrets not available. Set ANTHROPIC_OAUTH_TOKEN in your environment.");
+        }
+
+        // Make the token visible to `optional_env()` for subsequent config
+        // resolution (model selection step). Uses the thread-safe overlay
+        // instead of `std::env::set_var` to avoid UB on multi-threaded runtimes.
+        crate::config::inject_single_var("ANTHROPIC_OAUTH_TOKEN", token);
+
+        // Cache for model fetching
+        self.llm_api_key = Some(SecretString::from(token.to_string()));
+
+        print_success("Anthropic OAuth configured");
+        Ok(())
+    }
+
     /// Shared setup flow for API-key-based providers.
     async fn setup_api_key_provider(
         &mut self,
@@ -1052,6 +1164,11 @@ impl SetupWizard {
             ));
         }
 
+        // Make key visible to `optional_env()` for subsequent config resolution.
+        // Uses the thread-safe overlay instead of `std::env::set_var` to avoid
+        // UB on multi-threaded runtimes.
+        crate::config::inject_single_var(env_var, key_str);
+
         // Cache key in memory for model fetching later in the wizard
         self.llm_api_key = Some(SecretString::from(key_str.to_string()));
 
@@ -1988,6 +2105,67 @@ impl SetupWizard {
             }
         }
 
+        // Claude Code sandbox sub-step (only if Docker sandbox is enabled)
+        if self.settings.sandbox.enabled {
+            self.step_claude_code_sandbox().await?;
+        }
+
+        Ok(())
+    }
+
+    /// Claude Code sandbox sub-step: enable Claude CLI inside Docker containers.
+    async fn step_claude_code_sandbox(&mut self) -> Result<(), SetupError> {
+        println!();
+        print_info("Claude Code mode lets the agent delegate complex tasks to Claude CLI");
+        print_info("running inside sandboxed Docker containers.");
+        println!();
+
+        if !confirm("Enable Claude Code sandbox mode?", false).map_err(SetupError::Io)? {
+            self.settings.sandbox.claude_code_enabled = false;
+            return Ok(());
+        }
+
+        // Check for Anthropic credentials (API key or OAuth token).
+        // Uses `optional_env()` which reads both real env vars and the
+        // injected overlay (secrets DB, wizard-set values).
+        let has_credentials = || {
+            let has_api_key = crate::config::helpers::optional_env("ANTHROPIC_API_KEY")
+                .ok()
+                .flatten()
+                .is_some_and(|v| !v.is_empty() && v != OAUTH_PLACEHOLDER);
+            let has_oauth = crate::config::ClaudeCodeConfig::extract_oauth_token().is_some()
+                || crate::config::helpers::optional_env("ANTHROPIC_OAUTH_TOKEN")
+                    .ok()
+                    .flatten()
+                    .is_some_and(|v| !v.is_empty());
+            has_api_key || has_oauth
+        };
+
+        if has_credentials() {
+            self.settings.sandbox.claude_code_enabled = true;
+            print_success("Claude Code sandbox enabled");
+        } else {
+            print_error("No Anthropic credentials found.");
+            print_info(
+                "Claude Code needs ANTHROPIC_API_KEY or an OAuth token from `claude login`.",
+            );
+            println!();
+
+            if confirm("Retry after setting up credentials?", false).map_err(SetupError::Io)? {
+                if has_credentials() {
+                    self.settings.sandbox.claude_code_enabled = true;
+                    print_success("Claude Code sandbox enabled");
+                } else {
+                    self.settings.sandbox.claude_code_enabled = false;
+                    print_info("No credentials found. Claude Code disabled for now.");
+                    print_info("Set ANTHROPIC_API_KEY or run `claude login` and enable later.");
+                }
+            } else {
+                self.settings.sandbox.claude_code_enabled = false;
+                print_info("Claude Code disabled. Enable with CLAUDE_CODE_ENABLED=true later.");
+            }
+        }
+
         Ok(())
     }
 
@@ -2081,6 +2259,12 @@ impl SetupWizard {
     ///
     /// These are the chicken-and-egg settings needed before the database is
     /// connected (DATABASE_BACKEND, DATABASE_URL, LLM_BACKEND, etc.).
+    ///
+    /// **Credentials are NOT written here.** API keys and OAuth tokens live
+    /// only in the encrypted secrets DB. `LlmConfig::resolve()` defers
+    /// gracefully when credentials are missing during early startup, and the
+    /// re-resolution in `AppBuilder::build_all()` fills them in after
+    /// `inject_llm_keys_from_secrets()` loads from encrypted storage.
     fn write_bootstrap_env(&self) -> Result<(), SetupError> {
         let registry = crate::llm::ProviderRegistry::load();
         let mut env_vars: Vec<(String, String)> = Vec::new();
@@ -2146,6 +2330,11 @@ impl SetupWizard {
             env_vars.push(("ONBOARD_COMPLETED".to_string(), "true".to_string()));
         }
 
+        // Claude Code sandbox mode
+        if self.settings.sandbox.claude_code_enabled {
+            env_vars.push(("CLAUDE_CODE_ENABLED".to_string(), "true".to_string()));
+        }
+
         // Signal channel env vars (chicken-and-egg: config resolves before DB).
         if let Some(ref url) = self.settings.channels.signal_http_url {
             env_vars.push(("SIGNAL_HTTP_URL".to_string(), url.clone()));
@@ -2513,22 +2702,39 @@ async fn fetch_anthropic_models(cached_key: Option<&str>) -> Vec<(String, String
     let api_key = cached_key
         .map(String::from)
         .or_else(|| std::env::var("ANTHROPIC_API_KEY").ok())
-        .filter(|k| !k.is_empty());
+        .filter(|k| !k.is_empty() && k != crate::config::llm::OAUTH_PLACEHOLDER);
 
-    let api_key = match api_key {
+    // Fall back to OAuth token if no API key
-        Some(k) => k,
+    let oauth_token = if api_key.is_none() {
-        None => return static_defaults,
+        crate::config::helpers::optional_env("ANTHROPIC_OAUTH_TOKEN")
+            .ok()
+            .flatten()
+            .filter(|t| !t.is_empty())
+    } else {
+        None
+    };
+
+    let (key_or_token, is_oauth) = match (api_key, oauth_token) {
+        (Some(k), _) => (k, false),
+        (None, Some(t)) => (t, true),
+        (None, None) => return static_defaults,
     };
 
     let client = reqwest::Client::new();
-    let resp = match client
+    let mut request = client
         .get("https://api.anthropic.com/v1/models")
-        .header("x-api-key", &api_key)
         .header("anthropic-version", "2023-06-01")
-        .timeout(std::time::Duration::from_secs(5))
+        .timeout(std::time::Duration::from_secs(5));
-        .send()
+
-        .await
+    if is_oauth {
-    {
+        request = request
+            .bearer_auth(&key_or_token)
+            .header("anthropic-beta", "oauth-2025-04-20");
+    } else {
+        request = request.header("x-api-key", &key_or_token);
+    }
+
+    let resp = match request.send().await {
         Ok(r) if r.status().is_success() => r,
         _ => return static_defaults,
     };