diff --git a/pdm.lock b/pdm.lock
index d83da56..33edffc 100644
--- a/pdm.lock
+++ b/pdm.lock
@@ -5,7 +5,7 @@
 groups = ["default", "dev", "testing"]
 strategy = ["cross_platform", "inherit_metadata"]
 lock_version = "4.4.1"
-content_hash = "sha256:ff215917aa0a4f634788c7f83cab0540c5d5446b0b6d551af9ab635b03e14469"
+content_hash = "sha256:90a2e0d19ce5af6c64699269d1f82ca785c5ef752121c570efdee808a295bb3d"
 
 [[package]]
 name = "annotated-types"
@@ -1056,6 +1056,17 @@ files = [
     {file = "starlette-0.35.1.tar.gz", hash = "sha256:3e2639dac3520e4f58734ed22553f950d3f3cb1001cd2eaac4d57e8cdc5f66bc"},
 ]
 
+[[package]]
+name = "tenacity"
+version = "8.2.3"
+requires_python = ">=3.7"
+summary = "Retry code until it succeeds"
+groups = ["default"]
+files = [
+    {file = "tenacity-8.2.3-py3-none-any.whl", hash = "sha256:ce510e327a630c9e1beaf17d42e6ffacc88185044ad85cf74c0a8887c6a0f88c"},
+    {file = "tenacity-8.2.3.tar.gz", hash = "sha256:5398ef0d78e63f40007c1fb4c0bff96e1911394d2fa8d194f77619c05ff6cc8a"},
+]
+
 [[package]]
 name = "tomli"
 version = "2.0.1"
diff --git a/playground/generate_image.py b/playground/generate_image.py
index 12ea1e6..c16b703 100644
--- a/playground/generate_image.py
+++ b/playground/generate_image.py
@@ -38,6 +38,7 @@ async def main():
             session=globe_s, remove_sign=True
         )
     except APIError as e:
+        print(str(e))
         print(e.response)
         return
 
diff --git a/pyproject.toml b/pyproject.toml
index 497dd68..96e5d75 100644
--- a/pyproject.toml
+++ b/pyproject.toml
@@ -20,6 +20,7 @@ dependencies = [
     "argon2-cffi>=23.1.0",
     "opencv-python>=4.8.1.78",
     "fake-useragent>=1.4.0",
+    "tenacity>=8.2.3",
 ]
 requires-python = ">=3.8"
 readme = "README.md"
diff --git a/src/novelai_python/sdk/ai/generate_image/__init__.py b/src/novelai_python/sdk/ai/generate_image/__init__.py
index e9057af..cde9550 100644
--- a/src/novelai_python/sdk/ai/generate_image/__init__.py
+++ b/src/novelai_python/sdk/ai/generate_image/__init__.py
@@ -18,6 +18,7 @@
 from curl_cffi.requests import AsyncSession
 from loguru import logger
 from pydantic import BaseModel, ConfigDict, PrivateAttr, field_validator, model_validator, Field
+from tenacity import retry, stop_after_attempt, wait_random, retry_if_exception
 from typing_extensions import override
 
 from ._enum import Model, Sampler, NoiseSchedule, ControlNetModel, Action, UCPreset
@@ -327,6 +328,12 @@ async def necessary_headers(self, request_data) -> dict:
             "Cache-Control": "no-cache",
         }
 
+    @retry(
+        wait=wait_random(min=1, max=3),
+        stop=stop_after_attempt(3),
+        retry=retry_if_exception(lambda e: hasattr(e, "code") and str(e.code) == "500"),
+        reraise=True
+    )
     async def request(self,
                       session: Union[AsyncSession, "CredentialBase"],
                       *,
diff --git a/src/novelai_python/sdk/ai/upscale.py b/src/novelai_python/sdk/ai/upscale.py
index bdecb53..f21fb65 100644
--- a/src/novelai_python/sdk/ai/upscale.py
+++ b/src/novelai_python/sdk/ai/upscale.py
@@ -15,6 +15,7 @@
 from curl_cffi.requests import AsyncSession
 from loguru import logger
 from pydantic import ConfigDict, PrivateAttr, model_validator
+from tenacity import wait_random, retry, stop_after_attempt, retry_if_exception
 
 from ..schema import ApiBaseModel
 from ..._exceptions import APIError, AuthError, SessionHttpError
@@ -87,6 +88,12 @@ async def necessary_headers(self, request_data) -> dict:
             "Cache-Control": "no-cache",
         }
 
+    @retry(
+        wait=wait_random(min=1, max=3),
+        stop=stop_after_attempt(3),
+        retry=retry_if_exception(lambda e: hasattr(e, "code") and str(e.code) == "500"),
+        reraise=True
+    )
     async def request(self,
                       session: Union[AsyncSession, "CredentialBase"],
                       *,