diff --git a/CHANGELOG.md b/CHANGELOG.md
index 1bd4c0a1b..8aae0dc3c 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -104,6 +104,7 @@
 - Telegram: send GIF media as animations (auto-play) and improve filename sniffing.
 - Bash tool: inherit gateway PATH so Nix-provided tools resolve during commands. Thanks @joshp123 for PR #202.
 - Delivery chunking: keep Markdown fenced code blocks valid when splitting long replies (close + reopen fences).
+- Auth: prefer OAuth profiles over API keys during round-robin selection (prevents OAuth “lost after one message” when both are configured).
 
 ### Maintenance
 - Agent: add `skipBootstrap` config option. Thanks @onutc for PR #292.
diff --git a/src/agents/auth-profiles.test.ts b/src/agents/auth-profiles.test.ts
index 3b19dd8d5..f7fecba89 100644
--- a/src/agents/auth-profiles.test.ts
+++ b/src/agents/auth-profiles.test.ts
@@ -145,7 +145,7 @@ describe("resolveAuthProfileOrder", () => {
       },
       provider: "anthropic",
     });
-    expect(order).toEqual(["anthropic:b", "anthropic:a", "anthropic:c"]);
+    expect(order).toEqual(["anthropic:a", "anthropic:b", "anthropic:c"]);
   });
 
   it("pushes cooldown profiles to the end, ordered by cooldown expiry", () => {
diff --git a/src/agents/auth-profiles.ts b/src/agents/auth-profiles.ts
index 8722de5e5..8b0b31866 100644
--- a/src/agents/auth-profiles.ts
+++ b/src/agents/auth-profiles.ts
@@ -500,7 +500,7 @@ function orderProfilesByMode(
   }
 
   // Sort available profiles by lastUsed (oldest first = round-robin)
-  // Then by type (oauth preferred over api_key)
+  // Then by lastUsed (oldest first = round-robin within type)
   const scored = available.map((profileId) => {
     const type = store.profiles[profileId]?.type;
     const typeScore = type === "oauth" ? 0 : type === "api_key" ? 1 : 2;
@@ -508,14 +508,14 @@ function orderProfilesByMode(
     return { profileId, typeScore, lastUsed };
   });
 
-  // Primary sort: lastUsed (oldest first for round-robin)
-  // Secondary sort: type preference (oauth > api_key)
+  // Primary sort: type preference (oauth > api_key).
+  // Secondary sort: lastUsed (oldest first for round-robin within type).
   const sorted = scored
     .sort((a, b) => {
-      // First by lastUsed (oldest first)
-      if (a.lastUsed !== b.lastUsed) return a.lastUsed - b.lastUsed;
-      // Then by type
-      return a.typeScore - b.typeScore;
+      // First by type (oauth > api_key)
+      if (a.typeScore !== b.typeScore) return a.typeScore - b.typeScore;
+      // Then by lastUsed (oldest first)
+      return a.lastUsed - b.lastUsed;
     })
     .map((entry) => entry.profileId);