diff --git a/app/config.py b/app/config.py
index f794629e..2c0ff620 100644
--- a/app/config.py
+++ b/app/config.py
@@ -1,9 +1,9 @@
 #!/usr/bin/env python3
 
 import os
-from typing import List, Optional, Union
+from typing import Any, List, Optional, Union
 
-from pydantic import Field, field_validator
+from pydantic import Field, field_validator, model_validator
 from pydantic_settings import BaseSettings, SettingsConfigDict
 
 
@@ -267,6 +267,25 @@ class Settings(BaseSettings):
         description="Stricter rate limit for authentication endpoints to prevent brute force attacks.",
     )
 
+    @model_validator(mode="before")
+    @classmethod
+    def strip_outer_quotes(cls, data: Any) -> Any:
+        """
+        Strip matching surrounding quotes from string values.
+
+        In Kubernetes (and some other environments) env var values can arrive
+        with literal quote characters included, e.g. the value for DATABASE_URL
+        may be ``"postgresql://..."`` (with the quotes as part of the string)
+        rather than just ``postgresql://...``.  Docker Compose strips these
+        automatically; Kubernetes does not.
+        """
+        if isinstance(data, dict):
+            for key, value in data.items():
+                if isinstance(value, str) and len(value) >= 2:
+                    if (value[0] == '"' and value[-1] == '"') or (value[0] == "'" and value[-1] == "'"):
+                        data[key] = value[1:-1]
+        return data
+
     @field_validator("notification_urls", mode="before")
     @classmethod
     def parse_notification_urls(cls, v: str | list[str]) -> list[str]:
diff --git a/tests/test_config.py b/tests/test_config.py
index 86701feb..0faf4a96 100644
--- a/tests/test_config.py
+++ b/tests/test_config.py
@@ -289,3 +289,94 @@ class TestSecurityConfiguration:
 
         # Should not raise an error
         assert config.database_url == "sqlite:///test.db"
+
+
+# ---------------------------------------------------------------------------
+# Helpers shared across quote-stripping tests
+# ---------------------------------------------------------------------------
+
+_BASE_KWARGS = dict(
+    auth_enabled=False,
+    azure_ai_key="test",
+    azure_region="eastus",
+    azure_endpoint="https://test.example.com",
+    gotenberg_url="http://localhost:3000",
+    workdir="/tmp",
+    openai_api_key="sk-test",
+    redis_url="redis://localhost:6379",
+)
+
+
+@pytest.mark.unit
+class TestOuterQuoteStripping:
+    """
+    Tests that Settings strips surrounding quotes from string env var values.
+
+    In Kubernetes env vars can arrive with literal quote characters included
+    (e.g. DATABASE_URL="postgresql://..." with the quotes as part of the value).
+    Docker Compose strips these automatically; Kubernetes does not.
+    """
+
+    def test_double_quotes_stripped_from_url(self):
+        """Double-quoted URL value has quotes removed."""
+        config = Settings(
+            database_url='"sqlite:///test.db"',
+            **_BASE_KWARGS,
+        )
+        assert config.database_url == "sqlite:///test.db"
+
+    def test_single_quotes_stripped_from_url(self):
+        """Single-quoted URL value has quotes removed."""
+        config = Settings(
+            database_url="'sqlite:///test.db'",
+            **_BASE_KWARGS,
+        )
+        assert config.database_url == "sqlite:///test.db"
+
+    def test_double_quotes_stripped_from_optional_field(self):
+        """Quotes are stripped from optional string fields too."""
+        config = Settings(
+            database_url="sqlite:///test.db",
+            dropbox_app_key='"my-app-key"',
+            **_BASE_KWARGS,
+        )
+        assert config.dropbox_app_key == "my-app-key"
+
+    def test_unquoted_value_unchanged(self):
+        """Values without surrounding quotes are left as-is."""
+        config = Settings(
+            database_url="sqlite:///test.db",
+            **_BASE_KWARGS,
+        )
+        assert config.database_url == "sqlite:///test.db"
+
+    def test_mismatched_quotes_not_stripped(self):
+        """Mismatched quotes (open with one type, close with another) are NOT stripped."""
+        raw = '"sqlite:///test.db\''
+        config = Settings(
+            database_url=raw,
+            **_BASE_KWARGS,
+        )
+        assert config.database_url == raw
+
+    def test_single_quote_char_not_stripped(self):
+        """A single-character string that is just one quote is NOT modified."""
+        # A value of exactly one character cannot have matching outer quotes
+        config = Settings(
+            database_url="sqlite:///test.db",
+            openai_model='"',
+            **_BASE_KWARGS,
+        )
+        assert config.openai_model == '"'
+
+    def test_multiple_fields_stripped_simultaneously(self):
+        """Multiple quoted fields in the same config are all stripped."""
+        config = Settings(
+            database_url='"sqlite:///test.db"',
+            redis_url='"redis://localhost:6379"',
+            workdir='"/data/workdir"',
+            **{k: v for k, v in _BASE_KWARGS.items() if k not in ("redis_url", "workdir")},
+        )
+        assert config.database_url == "sqlite:///test.db"
+        assert config.redis_url == "redis://localhost:6379"
+        assert config.workdir == "/data/workdir"