diff --git a/pyproject.toml b/pyproject.toml
index f37aece9..355e8a12 100644
--- a/pyproject.toml
+++ b/pyproject.toml
@@ -32,7 +32,7 @@ dependencies = [
     "httpx>=0.28",
     "fastapi>=0.135",
     "uvicorn>=0.44",
-    "claude-agent-sdk>=0.1.63",
+    "claude-agent-sdk>=0.1.66",
     "Pillow>=10.0",
     # Federation crypto (sealed_box_v1): X25519, Ed25519, HKDF, XChaCha20-Poly1305.
     "cryptography>=41.0",
diff --git a/uv.lock b/uv.lock
index 3b6c1a22..68947ab6 100644
--- a/uv.lock
+++ b/uv.lock
@@ -508,19 +508,19 @@ wheels = [
 
 [[package]]
 name = "claude-agent-sdk"
-version = "0.1.63"
+version = "0.1.66"
 source = { registry = "https://pypi.org/simple" }
 dependencies = [
     { name = "anyio" },
     { name = "mcp" },
 ]
-sdist = { url = "https://files.pythonhosted.org/packages/80/03/83b5d0ab68430da8f0f3632dc3cf714a3d03f35fe57caaf89fb2c79fcdfd/claude_agent_sdk-0.1.63.tar.gz", hash = "sha256:c251c402667743ff0424edd35223ebba62dc5b29c6f22d35821fc13f807f75e7", size = 130409, upload-time = "2026-04-18T01:48:56.065Z" }
+sdist = { url = "https://files.pythonhosted.org/packages/81/74/ff47c188637e16a781afcc8419da487a4860ba6d8e4ad16ea29f40e99038/claude_agent_sdk-0.1.66.tar.gz", hash = "sha256:b8fb14198456f536f71733a4da84ec79c44d7f91b06ff34a4786087a1b043c48", size = 233308, upload-time = "2026-04-23T23:35:23.209Z" }
 wheels = [
-    { url = "https://files.pythonhosted.org/packages/82/af/a81aaddc31a8ca3998da796786dcff66ef92b7449442ab16132efeb86a3d/claude_agent_sdk-0.1.63-py3-none-macosx_11_0_arm64.whl", hash = "sha256:b57f312cb73bee7694ca1566aa2b045f53e01212ef815579d36128ddf839a684", size = 60290629, upload-time = "2026-04-18T01:48:59.222Z" },
-    { url = "https://files.pythonhosted.org/packages/30/65/62d11694242a1bd861f8e58f9db4f59b5cf560779ad9d3192a546e0b15a4/claude_agent_sdk-0.1.63-py3-none-macosx_11_0_x86_64.whl", hash = "sha256:9c4e13b621219b8d31d64eac103e2ce8a599aff44fe73dbf904248e5021ab0eb", size = 62110912, upload-time = "2026-04-18T01:49:02.808Z" },
-    { url = "https://files.pythonhosted.org/packages/b5/c1/93ab9672e98508778dae037713fd1d8f0bc197d44df6652df619c4715181/claude_agent_sdk-0.1.63-py3-none-manylinux_2_17_aarch64.whl", hash = "sha256:9cabf16c1ac034c3f557d31fd9aeae40e04bad7a71908d1d890f07bad38c6d19", size = 73559155, upload-time = "2026-04-18T01:49:09.389Z" },
-    { url = "https://files.pythonhosted.org/packages/ea/fd/22068e6dcf3d9f8951e11bddf654462efde24d696d3285bfe66411284eb0/claude_agent_sdk-0.1.63-py3-none-manylinux_2_17_x86_64.whl", hash = "sha256:c277c9f2855c2b162cbe5556d0a0ffe41943c506c2d8fed98147c5f9ee5f735c", size = 73691612, upload-time = "2026-04-18T01:49:12.757Z" },
-    { url = "https://files.pythonhosted.org/packages/f2/21/29b183534afbcdbaf1c876760146d6684c0cca68cb41a080ece15bdc37af/claude_agent_sdk-0.1.63-py3-none-win_amd64.whl", hash = "sha256:462eb63f748cb10ebb627349d2aac73b99eaa70daa6d2055ef16fe64b11f1d78", size = 75807487, upload-time = "2026-04-18T01:49:16.369Z" },
+    { url = "https://files.pythonhosted.org/packages/62/e0/a1f0e510b506dc3dd6da47eeaf1e750882d2ade11cda8f301a353290b671/claude_agent_sdk-0.1.66-py3-none-macosx_11_0_arm64.whl", hash = "sha256:18c35bdf52ba3c2a0a694fa3981484e5f5432e7c96cfbd76d70d73aef2a8b87e", size = 63218880, upload-time = "2026-04-23T23:35:27.679Z" },
+    { url = "https://files.pythonhosted.org/packages/9a/c1/f451c5168d98027665b2356b7baebbb898d5ab3bded41788e5c823790ba7/claude_agent_sdk-0.1.66-py3-none-macosx_11_0_x86_64.whl", hash = "sha256:c8281b0af9733bdcd4672dcc334006af6e5bf83098be38e66222feb9e32a0f41", size = 65184888, upload-time = "2026-04-23T23:35:31.932Z" },
+    { url = "https://files.pythonhosted.org/packages/59/40/49b81d04cc579e207676626eb777d7c99e566777fd696643db2c550c86ee/claude_agent_sdk-0.1.66-py3-none-manylinux_2_17_aarch64.whl", hash = "sha256:32536a6033dd6ea0fd63191389e77b4208f7ebafea8f8cb4d0befeff52e60a11", size = 76632992, upload-time = "2026-04-23T23:35:36.851Z" },
+    { url = "https://files.pythonhosted.org/packages/c9/17/5cd8da44188b115cd5b836d6bd293e242d7533c15aa9e4ad634024f9c182/claude_agent_sdk-0.1.66-py3-none-manylinux_2_17_x86_64.whl", hash = "sha256:10abd64e5f8dc65eb2f592c1d4db5607129ef983ecabdfd5ecf4b2692ee02293", size = 76610323, upload-time = "2026-04-23T23:35:42.639Z" },
+    { url = "https://files.pythonhosted.org/packages/90/fc/205a918b36e118370942e464578bb6637ffb2c749c63d8d1c634d4e3aefd/claude_agent_sdk-0.1.66-py3-none-win_amd64.whl", hash = "sha256:729984e3198bb62c96387b6c4bbe433eca2eb439abe5663c1bf1532e9e340d2b", size = 78346312, upload-time = "2026-04-23T23:35:48.219Z" },
 ]
 
 [[package]]
@@ -2257,7 +2257,7 @@ requires-dist = [
     { name = "beautifulsoup4", marker = "extra == 'web'", specifier = ">=4.12" },
     { name = "caldav", marker = "extra == 'calendar'", specifier = ">=1.3" },
     { name = "camoufox", marker = "extra == 'web'", specifier = ">=0.4" },
-    { name = "claude-agent-sdk", specifier = ">=0.1.63" },
+    { name = "claude-agent-sdk", specifier = ">=0.1.66" },
     { name = "cryptography", specifier = ">=41.0" },
     { name = "cryptography", marker = "extra == 'calendar'", specifier = ">=41.0" },
     { name = "discord-py", marker = "extra == 'discord'", specifier = ">=2.3" },