diff --git a/cli/medperf/account_management/account_management.py b/cli/medperf/account_management/account_management.py
index d19cf8cad..f8ea4e88e 100644
--- a/cli/medperf/account_management/account_management.py
+++ b/cli/medperf/account_management/account_management.py
@@ -19,16 +19,29 @@ def set_credentials(
     id_token_payload,
     token_issued_at,
     token_expires_in,
+    login_event=False,
 ):
     email = id_token_payload["email"]
     TokenStore().set_tokens(email, access_token, refresh_token)
+    config_p = read_config()
+
+    if login_event:
+        # Set the time the user logged in, so that we can track the lifetime of
+        # the refresh token
+        logged_in_at = token_issued_at
+    else:
+        # This means this is a refresh event. Preserve the logged_in_at timestamp.
+        logged_in_at = config_p.active_profile[config.credentials_keyword][
+            "logged_in_at"
+        ]
 
     account_info = {
         "email": email,
         "token_issued_at": token_issued_at,
         "token_expires_in": token_expires_in,
+        "logged_in_at": logged_in_at,
     }
-    config_p = read_config()
+
     config_p.active_profile[config.credentials_keyword] = account_info
     write_config(config_p)
 
diff --git a/cli/medperf/comms/auth/auth0.py b/cli/medperf/comms/auth/auth0.py
index bfb53be31..0a694d77a 100644
--- a/cli/medperf/comms/auth/auth0.py
+++ b/cli/medperf/comms/auth/auth0.py
@@ -66,6 +66,7 @@ def login(self, email):
             id_token_payload,
             token_issued_at,
             token_expires_in,
+            login_event=True,
         )
 
     def __request_device_code(self):
@@ -191,16 +192,30 @@ def _access_token(self):
         refresh_token = creds["refresh_token"]
         token_expires_in = creds["token_expires_in"]
         token_issued_at = creds["token_issued_at"]
-        leeway_time = token_issued_at + token_expires_in - config.token_expiration_leeway
-        absolute_expiration_time = token_issued_at + config.token_absolute_expiry
+        logged_in_at = creds["logged_in_at"]
+
+        # token_issued_at and expires_in are for the access token
+        sliding_expiration_time = (
+            token_issued_at + token_expires_in - config.token_expiration_leeway
+        )
+        absolute_expiration_time = (
+            logged_in_at
+            + config.token_absolute_expiry
+            - config.refresh_token_expiration_leeway
+        )
         current_time = time.time()
-        if current_time > leeway_time and current_time <= absolute_expiration_time:
-            access_token = self.__refresh_access_token(refresh_token)
-        elif current_time > absolute_expiration_time:
-            # Expired token. Force logout and ask the user to re-authenticate
-            logging.debug(f"Token expired: {absolute_expiration_time=} <> {current_time=}")
+        if current_time > absolute_expiration_time:
+            # Expired refresh token. Force logout and ask the user to re-authenticate
+            logging.debug(
+                f"Refresh token expired: {absolute_expiration_time=} <> {current_time=}"
+            )
             self.logout()
             raise AuthenticationError("Token expired. Please re-authenticate")
+
+        if current_time > sliding_expiration_time:
+            # Expired access token. Refresh it.
+            access_token = self.__refresh_access_token(refresh_token)
+
         return access_token
 
     def __refresh_access_token(self, refresh_token):
diff --git a/cli/medperf/config.py b/cli/medperf/config.py
index 3fc105c2e..2c5b520be 100644
--- a/cli/medperf/config.py
+++ b/cli/medperf/config.py
@@ -37,7 +37,8 @@
 auth_jwks_cache_ttl = 600  # fetch jwks every 10 mins. Default value in auth0 python SDK
 
 token_expiration_leeway = 10  # Refresh tokens 10 seconds before expiration
-token_absolute_expiry = 2592000  # Maximum lifetime of a given token. This value is set on auth0's configuration
+refresh_token_expiration_leeway = 10  # Logout users 10 seconds before absolute token expiration.
+token_absolute_expiry = 2592000  # Refresh token absolute expiration time (seconds). This value is set on auth0's configuration
 access_token_storage_id = "medperf_access_token"
 refresh_token_storage_id = "medperf_refresh_token"
 
diff --git a/cli/medperf/storage/__init__.py b/cli/medperf/storage/__init__.py
index acebb6f31..74e4e7962 100644
--- a/cli/medperf/storage/__init__.py
+++ b/cli/medperf/storage/__init__.py
@@ -1,5 +1,6 @@
 import os
 import shutil
+import time
 
 from medperf import config
 from medperf.config_management import read_config, write_config
@@ -25,6 +26,7 @@ def apply_configuration_migrations():
 
     config_p = read_config()
 
+    # Migration for moving the logs folder to a new location
     if "logs_folder" not in config_p.storage:
         return
 
@@ -35,4 +37,16 @@ def apply_configuration_migrations():
 
     del config_p.storage["logs_folder"]
 
+    # Migration for tracking the login timestamp (i.e., refresh token issuance timestamp)
+    if config.credentials_keyword in config_p.active_profile:
+        # So the user is logged in
+        if "logged_in_at" not in config_p.active_profile[config.credentials_keyword]:
+            # Apply migration. We will set it to the current time, since this
+            # will make sure they will not be logged out before the actual refresh
+            # token expiration (for a better user experience). However, currently logged
+            # in users will still face a confusing error when the refresh token expires.
+            config_p.active_profile[config.credentials_keyword][
+                "logged_in_at"
+            ] = time.time()
+
     write_config(config_p)