diff --git a/letta/schemas/environment_variables.py b/letta/schemas/environment_variables.py
index 81abfa35..5db1c28a 100644
--- a/letta/schemas/environment_variables.py
+++ b/letta/schemas/environment_variables.py
@@ -1,11 +1,15 @@
+import traceback
 from typing import Optional
 
 from pydantic import Field, model_validator
 
+from letta.log import get_logger
 from letta.schemas.enums import PrimitiveType
 from letta.schemas.letta_base import LettaBase, OrmMetadataBase
 from letta.schemas.secret import Secret
 
+logger = get_logger(__name__)
+
 
 # Base Environment Variable
 class EnvironmentVariableBase(OrmMetadataBase):
@@ -28,11 +32,23 @@ class EnvironmentVariableBase(OrmMetadataBase):
     def sync_value_and_value_enc(self):
         """Sync deprecated `value` field with `value_enc` for backward compatibility."""
         if self.value_enc and not self.value:
+            # ERROR: This should not happen - all code paths should populate value via async decryption
+            # Log error with stack trace to identify the caller that bypassed async decryption
+            logger.warning(
+                f"Sync decryption fallback triggered for env var key={self.key}. "
+                f"This indicates a code path that bypassed async decryption. Stack trace:\n{''.join(traceback.format_stack())}"
+            )
             # Decrypt value_enc -> value (for API responses)
             plaintext = self.value_enc.get_plaintext()
             if plaintext:
                 self.value = plaintext
         elif self.value and not self.value_enc:
+            # WARNING: This triggers sync encryption - should use async encryption where possible
+            # Log warning with stack trace to identify the caller
+            logger.warning(
+                f"Sync encryption fallback triggered for env var key={self.key}. "
+                f"This indicates a code path that bypassed async encryption. Stack trace:\n{''.join(traceback.format_stack())}"
+            )
             # Encrypt value -> value_enc (for backward compat when value is provided directly)
             self.value_enc = Secret.from_plaintext(self.value)
         return self