diff --git a/package.json b/package.json
index 4abe102f..2ecd6fee 100644
--- a/package.json
+++ b/package.json
@@ -26,6 +26,8 @@
     "@dnd-kit/core": "^6.0.8",
     "@dnd-kit/sortable": "^7.0.2",
     "@langchain/community": "^0.0.27",
+    "@langchain/core": "^0.1.57",
+    "@langchain/openai": "^0.0.28",
     "@radix-ui/react-dialog": "^1.0.3",
     "@radix-ui/react-dropdown-menu": "^2.0.4",
     "@radix-ui/react-select": "^2.0.0",
@@ -34,7 +36,7 @@
     "dnd-kit-sortable-tree": "^0.1.58",
     "endent": "^2.1.0",
     "jotai": "^2.4.3",
-    "langchain": "^0.1.17",
+    "langchain": "^0.1.33",
     "object-hash": "^3.0.0",
     "react": "^18.2.0",
     "react-dom": "^18.2.0",
diff --git a/src/components/Sidebar/auth/index.tsx b/src/components/Sidebar/auth/index.tsx
index b03595cd..c9ac860e 100644
--- a/src/components/Sidebar/auth/index.tsx
+++ b/src/components/Sidebar/auth/index.tsx
@@ -17,10 +17,9 @@ const Auth = () => {
   const handleOpenAiKeySubmit = async (e: React.FormEvent<HTMLFormElement>) => {
     e.preventDefault()
     const data = new FormData(e.currentTarget)
-    const key = data.get('openAiKey')
-    const isVaildApiKey: boolean = await validateApiKey(key as string)
+    const key = data.get('openAiKey') as string | null
 
-    if (key && isVaildApiKey) {
+    if (key && (await validateApiKey(key))) {
       setSettings((prev) => ({
         ...prev,
         chat: {
diff --git a/src/lib/validApiKey.ts b/src/lib/validApiKey.ts
index 4e88b5b2..2412c7b4 100644
--- a/src/lib/validApiKey.ts
+++ b/src/lib/validApiKey.ts
@@ -1,17 +1,16 @@
+import { HumanMessage } from '@langchain/core/messages'
 import axios from 'axios'
+import { ChatOpenAI } from 'langchain/chat_models/openai'
 
-const VERIFY_API_KEY_URL = 'https://api.openai.com/v1/models'
-
-export const validateApiKey = async (apiKey: string): Promise<boolean> => {
+export const validateApiKey = async (
+  openAIApiKey: string,
+): Promise<boolean> => {
+  const model = new ChatOpenAI({ openAIApiKey })
   try {
-    await axios.get(VERIFY_API_KEY_URL, {
-      headers: {
-        'Content-Type': 'application/json',
-        Authorization: `Bearer ${apiKey}`,
-      },
-    })
+    await model.invoke([new HumanMessage("Say Ok")])
     return true
-  } catch {
+  } catch (e) {
+    console.error(e)
     return false
   }
 }
diff --git a/yarn.lock b/yarn.lock
index 3ce373a5..0045d0c3 100644
--- a/yarn.lock
+++ b/yarn.lock
@@ -821,7 +821,7 @@
     "@jridgewell/resolve-uri" "3.1.0"
     "@jridgewell/sourcemap-codec" "1.4.14"
 
-"@langchain/community@^0.0.27", "@langchain/community@~0.0.20":
+"@langchain/community@^0.0.27":
   version "0.0.27"
   resolved "https://registry.yarnpkg.com/@langchain/community/-/community-0.0.27.tgz#910c33da06a21a635093c6f85d34ee1c31bc1bc0"
   integrity sha512-b/eV2MepDrGrImFbKdfiuhBYIQratKD45nILfmHpNJ4DFfs0RbCeZgyGBoIaVeIppnApkZmMGMisspjkDmJ+zA==
@@ -833,7 +833,38 @@
     uuid "^9.0.0"
     zod "^3.22.3"
 
-"@langchain/core@~0.1.13", "@langchain/core@~0.1.16", "@langchain/core@~0.1.25":
+"@langchain/community@~0.0.47":
+  version "0.0.48"
+  resolved "https://registry.yarnpkg.com/@langchain/community/-/community-0.0.48.tgz#a0a715f77d2a6914036c7b6fc32a760e1bf6bc9b"
+  integrity sha512-jG7dpJkgKtwbrSLsxW4mXmECopTj5tRt4+B+QcKCqZm7yEghFR44Xj5OkDWtzzsjpL47RJck5AJ8MsQnmi7WDQ==
+  dependencies:
+    "@langchain/core" "~0.1.56"
+    "@langchain/openai" "~0.0.28"
+    expr-eval "^2.0.2"
+    flat "^5.0.2"
+    langsmith "~0.1.1"
+    uuid "^9.0.0"
+    zod "^3.22.3"
+    zod-to-json-schema "^3.22.5"
+
+"@langchain/core@^0.1.57", "@langchain/core@~0.1.56":
+  version "0.1.57"
+  resolved "https://registry.yarnpkg.com/@langchain/core/-/core-0.1.57.tgz#c592ad6715e373e4203f590f20b8b999e64cfb16"
+  integrity sha512-6wOwidPkkRcANrOKl88+YYpm3jHfpg6W8EqZHQCImSAlxdEhyDSq2eeQKHOPCFCrfNWkClaNn+Wlzzz4Qwf9Tg==
+  dependencies:
+    ansi-styles "^5.0.0"
+    camelcase "6"
+    decamelize "1.2.0"
+    js-tiktoken "^1.0.8"
+    langsmith "~0.1.7"
+    ml-distance "^4.0.0"
+    p-queue "^6.6.2"
+    p-retry "4"
+    uuid "^9.0.0"
+    zod "^3.22.4"
+    zod-to-json-schema "^3.22.3"
+
+"@langchain/core@~0.1.13", "@langchain/core@~0.1.16":
   version "0.1.27"
   resolved "https://registry.yarnpkg.com/@langchain/core/-/core-0.1.27.tgz#a96e57180bf9ce8a118fa89573f3fb385e19f774"
   integrity sha512-I43G9r2NIs1qTjfU07D6PUGhCfc3anwziqDeoZ4mk2wphVv+8HhAbQNbOSvsuIk2p3qVkjXgxnI9cBFoEdwd0Q==
@@ -850,7 +881,18 @@
     zod "^3.22.4"
     zod-to-json-schema "^3.22.3"
 
-"@langchain/openai@~0.0.10", "@langchain/openai@~0.0.12":
+"@langchain/openai@^0.0.28", "@langchain/openai@~0.0.28":
+  version "0.0.28"
+  resolved "https://registry.yarnpkg.com/@langchain/openai/-/openai-0.0.28.tgz#afaeec61b44816935db9ae937496c964c81ab571"
+  integrity sha512-2s1RA3/eAnz4ahdzsMPBna9hfAqpFNlWdHiPxVGZ5yrhXsbLWWoPcF+22LCk9t0HJKtazi2GCIWc0HVXH9Abig==
+  dependencies:
+    "@langchain/core" "~0.1.56"
+    js-tiktoken "^1.0.7"
+    openai "^4.32.1"
+    zod "^3.22.4"
+    zod-to-json-schema "^3.22.3"
+
+"@langchain/openai@~0.0.10":
   version "0.0.14"
   resolved "https://registry.yarnpkg.com/@langchain/openai/-/openai-0.0.14.tgz#27a6ba83f6b754391868b22f3b90cd440038acf0"
   integrity sha512-co6nRylPrLGY/C3JYxhHt6cxLq07P086O7K3QaZH7SFFErIN9wSzJonpvhZR07DEUq6eK6wKgh2ORxA/NcjSRQ==
@@ -3933,22 +3975,21 @@ kleur@^4.0.3, kleur@^4.1.5:
   resolved "https://registry.yarnpkg.com/kleur/-/kleur-4.1.5.tgz#95106101795f7050c6c650f350c683febddb1780"
   integrity sha512-o+NO+8WrRiQEE4/7nwRJhN1HWpVmJm511pBHUxPLtp0BUISzlBplORYSmTclCnJvQq2tKu/sgl3xVpkc7ZWuQQ==
 
-langchain@^0.1.17:
-  version "0.1.17"
-  resolved "https://registry.yarnpkg.com/langchain/-/langchain-0.1.17.tgz#050732e56e1457f3c69bcf9de88981860a2237cd"
-  integrity sha512-w+fSAxsPdeMpJMhbS1Ur/dRhgRvw4j/vqD5kgfgmZNAh5X3nz5BXktcsyH8hwXLjuoFJMUyp3mIFy60APrY0Vw==
+langchain@^0.1.33:
+  version "0.1.33"
+  resolved "https://registry.yarnpkg.com/langchain/-/langchain-0.1.33.tgz#959f0f023975092569b49f1f07fe60c11c643530"
+  integrity sha512-IrRd839x8eAmDutHNDMHGzIjufyWt/ckJrnRB2WifIJmtLWNRNQo5jZd7toeBU0UOVOQxoPtQGYf8lR0ar7vIQ==
   dependencies:
     "@anthropic-ai/sdk" "^0.9.1"
-    "@langchain/community" "~0.0.20"
-    "@langchain/core" "~0.1.25"
-    "@langchain/openai" "~0.0.12"
+    "@langchain/community" "~0.0.47"
+    "@langchain/core" "~0.1.56"
+    "@langchain/openai" "~0.0.28"
     binary-extensions "^2.2.0"
-    expr-eval "^2.0.2"
     js-tiktoken "^1.0.7"
     js-yaml "^4.1.0"
     jsonpointer "^5.0.1"
-    langchainhub "~0.0.6"
-    langsmith "~0.0.59"
+    langchainhub "~0.0.8"
+    langsmith "~0.1.7"
     ml-distance "^4.0.0"
     openapi-types "^12.1.3"
     p-retry "4"
@@ -3957,10 +3998,10 @@ langchain@^0.1.17:
     zod "^3.22.4"
     zod-to-json-schema "^3.22.3"
 
-langchainhub@~0.0.6:
-  version "0.0.6"
-  resolved "https://registry.yarnpkg.com/langchainhub/-/langchainhub-0.0.6.tgz#9d2d06e4ce0807b4e8a31e19611f57aef990b54d"
-  integrity sha512-SW6105T+YP1cTe0yMf//7kyshCgvCTyFBMTgH2H3s9rTAR4e+78DA/BBrUL/Mt4Q5eMWui7iGuAYb3pgGsdQ9w==
+langchainhub@~0.0.8:
+  version "0.0.8"
+  resolved "https://registry.yarnpkg.com/langchainhub/-/langchainhub-0.0.8.tgz#fd4b96dc795e22e36c1a20bad31b61b0c33d3110"
+  integrity sha512-Woyb8YDHgqqTOZvWIbm2CaFDGfZ4NTSyXV687AG4vXEfoNo7cGQp7nhl7wL3ehenKWmNEmcxCLgOZzW8jE6lOQ==
 
 langsmith@~0.0.48:
   version "0.0.48"
@@ -3973,10 +4014,10 @@ langsmith@~0.0.48:
     p-retry "4"
     uuid "^9.0.0"
 
-langsmith@~0.0.59:
-  version "0.0.68"
-  resolved "https://registry.yarnpkg.com/langsmith/-/langsmith-0.0.68.tgz#8748d3203d348cc19e5ee4ddeef908964a62e21a"
-  integrity sha512-bxaJndEhUFDfv5soWKxONrLMZaVZfS+G4smJl3WYQlsEph8ierG3QbJfx1PEwl40TD0aFBjzq62usUX1UOCjuA==
+langsmith@~0.1.1, langsmith@~0.1.7:
+  version "0.1.14"
+  resolved "https://registry.yarnpkg.com/langsmith/-/langsmith-0.1.14.tgz#2b889dbcfb49547614df276a4a5a063092a1585d"
+  integrity sha512-iEzQLLB7/0nRpAwNBAR7B7N64fyByg5UsNjSvLaCCkQ9AS68PSafjB8xQkyI8QXXrGjU1dEqDRoa8m4SUuRdUw==
   dependencies:
     "@types/uuid" "^9.0.1"
     commander "^10.0.1"
@@ -4871,6 +4912,20 @@ openai@^4.26.0:
     node-fetch "^2.6.7"
     web-streams-polyfill "^3.2.1"
 
+openai@^4.32.1:
+  version "4.33.1"
+  resolved "https://registry.yarnpkg.com/openai/-/openai-4.33.1.tgz#7f14c28ea0994ff6eacc2dbca2131c61e7692cd4"
+  integrity sha512-0DH572aSxGTT1JPOXgJQ9mjiuSPg/7scPot8hLc5I1mfQxPxLXTZWJpWerKaIWOuPkR2nrB0SamGDEehH8RuWA==
+  dependencies:
+    "@types/node" "^18.11.18"
+    "@types/node-fetch" "^2.6.4"
+    abort-controller "^3.0.0"
+    agentkeepalive "^4.2.1"
+    form-data-encoder "1.7.2"
+    formdata-node "^4.3.2"
+    node-fetch "^2.6.7"
+    web-streams-polyfill "^3.2.1"
+
 openapi-types@^12.1.3:
   version "12.1.3"
   resolved "https://registry.yarnpkg.com/openapi-types/-/openapi-types-12.1.3.tgz#471995eb26c4b97b7bd356aacf7b91b73e777dd3"
@@ -6618,6 +6673,11 @@ zod-to-json-schema@^3.22.3:
   resolved "https://registry.yarnpkg.com/zod-to-json-schema/-/zod-to-json-schema-3.22.4.tgz#f8cc691f6043e9084375e85fb1f76ebafe253d70"
   integrity sha512-2Ed5dJ+n/O3cU383xSY28cuVi0BCQhF8nYqWU5paEpl7fVdqdAmiLdqLyfblbNdfOFwFfi/mqU4O1pwc60iBhQ==
 
+zod-to-json-schema@^3.22.5:
+  version "3.22.5"
+  resolved "https://registry.yarnpkg.com/zod-to-json-schema/-/zod-to-json-schema-3.22.5.tgz#3646e81cfc318dbad2a22519e5ce661615418673"
+  integrity sha512-+akaPo6a0zpVCCseDed504KBJUQpEW5QZw7RMneNmKw+fGaML1Z9tUNLnHHAC8x6dzVRO1eB2oEMyZRnuBZg7Q==
+
 zod@^3.22.3, zod@^3.22.4:
   version "3.22.4"
   resolved "https://registry.yarnpkg.com/zod/-/zod-3.22.4.tgz#f31c3a9386f61b1f228af56faa9255e845cf3fff"