diff --git a/apricot/apricot_server.py b/apricot/apricot_server.py
index 4d3978d..0cca36c 100644
--- a/apricot/apricot_server.py
+++ b/apricot/apricot_server.py
@@ -32,7 +32,7 @@ def __init__(
                 **kwargs,
             )
         except Exception as exc:
-            msg = f"Could not construct an OAuth client for the '{backend}' backend."
+            msg = f"Could not construct an OAuth client for the '{backend}' backend.\n{exc!s}"
             raise ValueError(msg) from exc
 
         # Create an LDAPServerFactory
diff --git a/apricot/ldap/oauth_ldap_server_factory.py b/apricot/ldap/oauth_ldap_server_factory.py
index 9794d1c..333eda8 100644
--- a/apricot/ldap/oauth_ldap_server_factory.py
+++ b/apricot/ldap/oauth_ldap_server_factory.py
@@ -19,6 +19,9 @@ def __init__(self, oauth_client: OAuthClient):
         # Create an LDAP lookup tree
         self.adaptor = OAuthLDAPTree(oauth_client)
 
+    def __repr__(self) -> str:
+        return f"{self.__class__.__name__} using adaptor {self.adaptor}"
+
     def buildProtocol(self, addr: IAddress) -> Protocol:  # noqa: N802
         """
         Create an LDAPServer instance.
diff --git a/apricot/ldap/oauth_ldap_tree.py b/apricot/ldap/oauth_ldap_tree.py
index 11adfd8..aa81313 100644
--- a/apricot/ldap/oauth_ldap_tree.py
+++ b/apricot/ldap/oauth_ldap_tree.py
@@ -37,6 +37,9 @@ def __init__(self, oauth_client: OAuthClient) -> None:
         for user_attrs in self.oauth_client.users():
             users_ou.add_child(f"CN={user_attrs['name'][0]}", user_attrs)
 
+    def __repr__(self) -> str:
+        return f"{self.__class__.__name__} with backend {self.oauth_client.__class__.__name__}"
+
     def build_root(self, dn: str, attributes: LDAPAttributeDict) -> OAuthLDAPEntry:
         """
         Construct the root of the LDAP tree
diff --git a/apricot/oauth/oauth_client.py b/apricot/oauth/oauth_client.py
index 3f1f24b..d3dcdb3 100644
--- a/apricot/oauth/oauth_client.py
+++ b/apricot/oauth/oauth_client.py
@@ -33,25 +33,40 @@ def __init__(
         # this, but Requests-OAuthlib raises exception on scope mismatch by default.)
         os.environ["OAUTHLIB_RELAX_TOKEN_SCOPE"] = "1"  # noqa: S105
         os.environ["OAUTHLIB_IGNORE_SCOPE_CHANGE"] = "1"
-        # OAuth client that uses application credentials
-        self.session_application = OAuth2Session(
-            client=BackendApplicationClient(
-                client_id=client_id, scope=scopes, redirect_uri=redirect_uri
+
+        try:
+            # OAuth client that uses application credentials
+            self.session_application = OAuth2Session(
+                client=BackendApplicationClient(
+                    client_id=client_id, scope=scopes, redirect_uri=redirect_uri
+                )
             )
-        )
-        # OAuth client that uses delegated credentials
-        self.session_interactive = OAuth2Session(
-            client=LegacyApplicationClient(
-                client_id=client_id, scope=scopes, redirect_uri=redirect_uri
+        except Exception as exc:
+            msg = f"Failed to initialise application credential client.\n{exc!s}"
+            raise RuntimeError(msg) from exc
+
+        try:
+            # OAuth client that uses delegated credentials
+            self.session_interactive = OAuth2Session(
+                client=LegacyApplicationClient(
+                    client_id=client_id, scope=scopes, redirect_uri=redirect_uri
+                )
             )
-        )
-        # Request a new bearer token
-        json_response = self.session_application.fetch_token(
-            token_url=self.token_url,
-            client_id=self.session_application._client.client_id,
-            client_secret=self.client_secret,
-        )
-        self.bearer_token = self.extract_token(json_response)
+        except Exception as exc:
+            msg = f"Failed to initialise delegated credential client.\n{exc!s}"
+            raise RuntimeError(msg) from exc
+
+        try:
+            # Request a new bearer token
+            json_response = self.session_application.fetch_token(
+                token_url=self.token_url,
+                client_id=self.session_application._client.client_id,
+                client_secret=self.client_secret,
+            )
+            self.bearer_token = self.extract_token(json_response)
+        except Exception as exc:
+            msg = f"Failed to fetch bearer token from OAuth endpoint.\n{exc!s}"
+            raise RuntimeError(msg) from exc
 
     @abstractmethod
     def extract_token(self, json_response: JSONDict) -> str:
diff --git a/run.py b/run.py
index 466958a..e1eeb6b 100644
--- a/run.py
+++ b/run.py
@@ -1,4 +1,5 @@
 import argparse
+import sys
 
 from apricot import ApricotServer
 from apricot.oauth import OAuthBackend
@@ -23,9 +24,10 @@
 
         # Create the Apricot server
         reactor = ApricotServer(**vars(args))
-    except Exception:
-        msg = "Unable to initialise Apricot server from provided command line arguments."
-        raise ValueError(msg)
+    except Exception as exc:
+        msg = f"Unable to initialise Apricot server from provided command line arguments.\n{str(exc)}"
+        print(msg)
+        sys.exit(1)
 
     # Run the Apricot server
     reactor.run()