diff --git a/authentication/api.py b/authentication/api.py
index 6a3135e5..8d5ee436 100644
--- a/authentication/api.py
+++ b/authentication/api.py
@@ -2,6 +2,7 @@
 
 import logging
 
+import requests
 from django.conf import settings
 from django.contrib.auth import get_user_model
 from oauthlib.oauth2 import (
@@ -45,8 +46,7 @@ def keycloak_session_init(url, **kwargs):
     }
 
     def update_token(token):
-        log_str = f"Refreshing Keycloak token {token}"
-        log.debug(log_str)
+        log.debug("Refreshing Keycloak token %s", {token})
         KeycloakAdminToken.objects.all().delete()
         KeycloakAdminToken.objects.create(
             authorization_token=token.get("access_token"),
@@ -59,18 +59,59 @@ def check_for_token():
         token = KeycloakAdminToken.latest()
 
         if not token:
-            this_dumb_message_because_ruff_is_annoying = "No token found"
-            raise TokenExpiredError(this_dumb_message_because_ruff_is_annoying)
+            token_error_msg = "No token found"  # noqa: S105
+            raise TokenExpiredError(token_error_msg)
 
         return token
 
-    # Note: we call get_user_info here in both the try and the except because you won't
-    # get a token error until you attempt to make a request.
+    def regenerate_token(client, token):
+        """Regenerate the token, or raise an exception."""
+
+        try:
+            session = OAuth2Session(client=client)
+            token = session.fetch_token(
+                token_url=token_url,
+                client_id=settings.KEYCLOAK_ADMIN_CLIENT_ID,
+                client_secret=settings.KEYCLOAK_ADMIN_CLIENT_SECRET,
+                verify=False,
+            )
+
+            update_token(token)
+            session = OAuth2Session(client=client, token=token)
+        except InvalidGrantError:
+            log.exception(
+                (
+                    "keycloak_session_init couldn't refresh token %s because of an"
+                    " invalid grant error"
+                ),
+                {token},
+            )
+            return None
+        except TokenExpiredError:
+            log.exception(
+                (
+                    "keycloak_session_init couldn't refresh token %s because of an"
+                    " expired token error"
+                ),
+                {token},
+            )
+            return None
+        except requests.exceptions.RequestException:
+            log.exception(
+                (
+                    "keycloak_session_init couldn't refresh token %s because of an"
+                    " HTTP error"
+                ),
+                {token},
+            )
+            return None
+
+        return session
+
     try:
         token = check_for_token()
 
-        log_str = f"Trying to start up a session with token {token.token_formatted}"
-        log.debug(log_str)
+        log.debug("Trying to start up a session with token %s", {token.token_formatted})
 
         session = OAuth2Session(
             client=client,
@@ -82,23 +123,22 @@ def check_for_token():
 
         keycloak_response = session.get(url, **kwargs).json()
     except (InvalidGrantError, TokenExpiredError) as ige:
-        log_str = f"Token error, trying to get a new token: {ige}"
-        log.debug(log_str)
-
-        session = OAuth2Session(client=client)
-        token = session.fetch_token(
-            token_url=token_url,
-            client_id=settings.KEYCLOAK_ADMIN_CLIENT_ID,
-            client_secret=settings.KEYCLOAK_ADMIN_CLIENT_SECRET,
-            verify=False,
-        )
+        log.debug("Token error, trying to get a new token: %s", {ige})
+
+        session = regenerate_token(client, token)
 
-        update_token(token)
-        session = OAuth2Session(client=client, token=token)
         keycloak_response = session.get(url, **kwargs).json()
+    except requests.exceptions.RequestException:
+        log.exception(
+            (
+                "keycloak_session_init couldn't establish the session because of"
+                " an HTTP error: %s"
+            ),
+            {token},
+        )
+        return None
 
-    log_str = f"Keycloak response: {keycloak_response}"
-    log.debug(log_str)
+    log.debug("Keycloak response: %s", {keycloak_response})
 
     return keycloak_response