diff --git a/skyvern/forge/sdk/services/bitwarden.py b/skyvern/forge/sdk/services/bitwarden.py
index 0465307fe..94b68c0de 100644
--- a/skyvern/forge/sdk/services/bitwarden.py
+++ b/skyvern/forge/sdk/services/bitwarden.py
@@ -41,6 +41,21 @@ def run_command(command: list[str], additional_env: dict[str, str] | None = None
 
         return subprocess.run(command, capture_output=True, text=True, env=env)
 
+    @staticmethod
+    def _extract_session_key(unlock_cmd_output: str) -> str | None:
+        # Split the text by lines
+        lines = unlock_cmd_output.split("\n")
+
+        # Look for the line containing the BW_SESSION
+        for line in lines:
+            if 'BW_SESSION="' in line:
+                # Find the start and end positions of the session key
+                start = line.find('BW_SESSION="') + len('BW_SESSION="')
+                end = line.rfind('"', start)
+                return line[start:end]
+
+        return None
+
     @staticmethod
     def get_secret_value_from_url(
         client_id: str,
@@ -61,25 +76,42 @@ def get_secret_value_from_url(
             login_command = ["bw", "login", "--apikey"]
             login_result = BitwardenService.run_command(login_command, env)
 
-            # Print both stdout and stderr for debugging
+            # Validate the login result
+            if login_result.stdout and "You are logged in!" not in login_result.stdout:
+                raise BitwardenLoginError(
+                    f"Failed to log in. stdout: {login_result.stdout} stderr: {login_result.stderr}"
+                )
+
             if login_result.stderr and "You are already logged in as" not in login_result.stderr:
-                raise BitwardenLoginError(login_result.stderr)
+                raise BitwardenLoginError(
+                    f"Failed to log in. stdout: {login_result.stdout} stderr: {login_result.stderr}"
+                )
+
+            LOG.info("Bitwarden login successful")
 
             # Step 2: Unlock the vault
             unlock_command = ["bw", "unlock", "--passwordenv", "BW_PASSWORD"]
             unlock_result = BitwardenService.run_command(unlock_command, env)
 
+            # Validate the unlock result
+            if unlock_result.stdout and "Your vault is now unlocked!" not in unlock_result.stdout:
+                raise BitwardenUnlockError(
+                    f"Failed to unlock vault. stdout: {unlock_result.stdout} stderr: {unlock_result.stderr}"
+                )
+
             # This is a part of Bitwarden's client-side telemetry
             # TODO -- figure out how to disable this telemetry so we never get this error
             # https://github.com/bitwarden/clients/blob/9d10825dbd891c0f41fe1b4c4dd3ca4171f63be5/libs/common/src/services/api.service.ts#L1473
             if unlock_result.stderr and "Event post failed" not in unlock_result.stderr:
-                raise BitwardenUnlockError(unlock_result.stderr)
+                raise BitwardenUnlockError(
+                    f"Failed to unlock vault. stdout: {unlock_result.stdout} stderr: {unlock_result.stderr}"
+                )
 
             # Extract session key
             try:
-                session_key = unlock_result.stdout.split('"')[1]
-            except IndexError:
-                raise BitwardenUnlockError("Unable to extract session key.")
+                session_key = BitwardenService._extract_session_key(unlock_result.stdout)
+            except Exception as e:
+                raise BitwardenUnlockError(f"Unable to extract session key: {str(e)}")
 
             if not session_key:
                 raise BitwardenUnlockError("Session key is empty.")