diff --git a/changelog.d/8874.feature b/changelog.d/8874.feature
new file mode 100644
index 000000000..720665eca
--- /dev/null
+++ b/changelog.d/8874.feature
@@ -0,0 +1 @@
+Improve the error messages printed as a result of configuration problems for extension modules.
diff --git a/synapse/app/homeserver.py b/synapse/app/homeserver.py
index 2b5465417..bbb740783 100644
--- a/synapse/app/homeserver.py
+++ b/synapse/app/homeserver.py
@@ -19,7 +19,7 @@ import gc
 import logging
 import os
 import sys
-from typing import Iterable
+from typing import Iterable, Iterator
 
 from twisted.application import service
 from twisted.internet import defer, reactor
@@ -90,7 +90,7 @@ class SynapseHomeServer(HomeServer):
         tls = listener_config.tls
         site_tag = listener_config.http_options.tag
         if site_tag is None:
-            site_tag = port
+            site_tag = str(port)
 
         # We always include a health resource.
         resources = {"/health": HealthResource()}
@@ -107,7 +107,10 @@ class SynapseHomeServer(HomeServer):
         logger.debug("Configuring additional resources: %r", additional_resources)
         module_api = self.get_module_api()
         for path, resmodule in additional_resources.items():
-            handler_cls, config = load_module(resmodule)
+            handler_cls, config = load_module(
+                resmodule,
+                ("listeners", site_tag, "additional_resources", "<%s>" % (path,)),
+            )
             handler = handler_cls(config, module_api)
             if IResource.providedBy(handler):
                 resource = handler
@@ -342,7 +345,10 @@ def setup(config_options):
             "Synapse Homeserver", config_options
         )
     except ConfigError as e:
-        sys.stderr.write("\nERROR: %s\n" % (e,))
+        sys.stderr.write("\n")
+        for f in format_config_error(e):
+            sys.stderr.write(f)
+        sys.stderr.write("\n")
         sys.exit(1)
 
     if not config:
@@ -445,6 +451,38 @@ def setup(config_options):
     return hs
 
 
+def format_config_error(e: ConfigError) -> Iterator[str]:
+    """
+    Formats a config error neatly
+
+    The idea is to format the immediate error, plus the "causes" of those errors,
+    hopefully in a way that makes sense to the user. For example:
+
+        Error in configuration at 'oidc_config.user_mapping_provider.config.display_name_template':
+          Failed to parse config for module 'JinjaOidcMappingProvider':
+            invalid jinja template:
+              unexpected end of template, expected 'end of print statement'.
+
+    Args:
+        e: the error to be formatted
+
+    Returns: An iterator which yields string fragments to be formatted
+    """
+    yield "Error in configuration"
+
+    if e.path:
+        yield " at '%s'" % (".".join(e.path),)
+
+    yield ":\n  %s" % (e.msg,)
+
+    e = e.__cause__
+    indent = 1
+    while e:
+        indent += 1
+        yield ":\n%s%s" % ("  " * indent, str(e))
+        e = e.__cause__
+
+
 class SynapseService(service.Service):
     """
     A twisted Service class that will start synapse. Used to run synapse
diff --git a/synapse/config/_base.py b/synapse/config/_base.py
index 85f65da4d..2931a8820 100644
--- a/synapse/config/_base.py
+++ b/synapse/config/_base.py
@@ -23,7 +23,7 @@ import urllib.parse
 from collections import OrderedDict
 from hashlib import sha256
 from textwrap import dedent
-from typing import Any, Callable, List, MutableMapping, Optional
+from typing import Any, Callable, Iterable, List, MutableMapping, Optional
 
 import attr
 import jinja2
@@ -32,7 +32,17 @@ import yaml
 
 
 class ConfigError(Exception):
-    pass
+    """Represents a problem parsing the configuration
+
+    Args:
+        msg:  A textual description of the error.
+        path: Where appropriate, an indication of where in the configuration
+           the problem lies.
+    """
+
+    def __init__(self, msg: str, path: Optional[Iterable[str]] = None):
+        self.msg = msg
+        self.path = path
 
 
 # We split these messages out to allow packages to override with package
diff --git a/synapse/config/_base.pyi b/synapse/config/_base.pyi
index b8faafa9b..ed26e2fb6 100644
--- a/synapse/config/_base.pyi
+++ b/synapse/config/_base.pyi
@@ -1,4 +1,4 @@
-from typing import Any, List, Optional
+from typing import Any, Iterable, List, Optional
 
 from synapse.config import (
     api,
@@ -35,7 +35,10 @@ from synapse.config import (
     workers,
 )
 
-class ConfigError(Exception): ...
+class ConfigError(Exception):
+    def __init__(self, msg: str, path: Optional[Iterable[str]] = None):
+        self.msg = msg
+        self.path = path
 
 MISSING_REPORT_STATS_CONFIG_INSTRUCTIONS: str
 MISSING_REPORT_STATS_SPIEL: str
diff --git a/synapse/config/_util.py b/synapse/config/_util.py
index c74969a97..1bbe83c31 100644
--- a/synapse/config/_util.py
+++ b/synapse/config/_util.py
@@ -38,14 +38,27 @@ def validate_config(
     try:
         jsonschema.validate(config, json_schema)
     except jsonschema.ValidationError as e:
-        # copy `config_path` before modifying it.
-        path = list(config_path)
-        for p in list(e.path):
-            if isinstance(p, int):
-                path.append("<item %i>" % p)
-            else:
-                path.append(str(p))
+        raise json_error_to_config_error(e, config_path)
 
-        raise ConfigError(
-            "Unable to parse configuration: %s at %s" % (e.message, ".".join(path))
-        )
+
+def json_error_to_config_error(
+    e: jsonschema.ValidationError, config_path: Iterable[str]
+) -> ConfigError:
+    """Converts a json validation error to a user-readable ConfigError
+
+    Args:
+        e: the exception to be converted
+        config_path: the path within the config file. This will be used as a basis
+           for the error message.
+
+    Returns:
+        a ConfigError
+    """
+    # copy `config_path` before modifying it.
+    path = list(config_path)
+    for p in list(e.path):
+        if isinstance(p, int):
+            path.append("<item %i>" % p)
+        else:
+            path.append(str(p))
+    return ConfigError(e.message, path)
diff --git a/synapse/config/oidc_config.py b/synapse/config/oidc_config.py
index 69d188341..1abf8ed40 100644
--- a/synapse/config/oidc_config.py
+++ b/synapse/config/oidc_config.py
@@ -66,7 +66,7 @@ class OIDCConfig(Config):
         (
             self.oidc_user_mapping_provider_class,
             self.oidc_user_mapping_provider_config,
-        ) = load_module(ump_config)
+        ) = load_module(ump_config, ("oidc_config", "user_mapping_provider"))
 
         # Ensure loaded user mapping module has defined all necessary methods
         required_methods = [
diff --git a/synapse/config/password_auth_providers.py b/synapse/config/password_auth_providers.py
index 4fda8ae98..85d07c4f8 100644
--- a/synapse/config/password_auth_providers.py
+++ b/synapse/config/password_auth_providers.py
@@ -36,7 +36,7 @@ class PasswordAuthProviderConfig(Config):
             providers.append({"module": LDAP_PROVIDER, "config": ldap_config})
 
         providers.extend(config.get("password_providers") or [])
-        for provider in providers:
+        for i, provider in enumerate(providers):
             mod_name = provider["module"]
 
             # This is for backwards compat when the ldap auth provider resided
@@ -45,7 +45,8 @@ class PasswordAuthProviderConfig(Config):
                 mod_name = LDAP_PROVIDER
 
             (provider_class, provider_config) = load_module(
-                {"module": mod_name, "config": provider["config"]}
+                {"module": mod_name, "config": provider["config"]},
+                ("password_providers", "<item %i>" % i),
             )
 
             self.password_providers.append((provider_class, provider_config))
diff --git a/synapse/config/repository.py b/synapse/config/repository.py
index ba1e9d236..17ce9145e 100644
--- a/synapse/config/repository.py
+++ b/synapse/config/repository.py
@@ -142,7 +142,7 @@ class ContentRepositoryConfig(Config):
         # them to be started.
         self.media_storage_providers = []  # type: List[tuple]
 
-        for provider_config in storage_providers:
+        for i, provider_config in enumerate(storage_providers):
             # We special case the module "file_system" so as not to need to
             # expose FileStorageProviderBackend
             if provider_config["module"] == "file_system":
@@ -151,7 +151,9 @@ class ContentRepositoryConfig(Config):
                     ".FileStorageProviderBackend"
                 )
 
-            provider_class, parsed_config = load_module(provider_config)
+            provider_class, parsed_config = load_module(
+                provider_config, ("media_storage_providers", "<item %i>" % i)
+            )
 
             wrapper_config = MediaStorageProviderConfig(
                 provider_config.get("store_local", False),
diff --git a/synapse/config/room_directory.py b/synapse/config/room_directory.py
index 92e1b6752..9a3e1c3e7 100644
--- a/synapse/config/room_directory.py
+++ b/synapse/config/room_directory.py
@@ -180,7 +180,7 @@ class _RoomDirectoryRule:
             self._alias_regex = glob_to_regex(alias)
             self._room_id_regex = glob_to_regex(room_id)
         except Exception as e:
-            raise ConfigError("Failed to parse glob into regex: %s", e)
+            raise ConfigError("Failed to parse glob into regex") from e
 
     def matches(self, user_id, room_id, aliases):
         """Tests if this rule matches the given user_id, room_id and aliases.
diff --git a/synapse/config/saml2_config.py b/synapse/config/saml2_config.py
index c1b8e98ae..7b97d4f11 100644
--- a/synapse/config/saml2_config.py
+++ b/synapse/config/saml2_config.py
@@ -125,7 +125,7 @@ class SAML2Config(Config):
         (
             self.saml2_user_mapping_provider_class,
             self.saml2_user_mapping_provider_config,
-        ) = load_module(ump_dict)
+        ) = load_module(ump_dict, ("saml2_config", "user_mapping_provider"))
 
         # Ensure loaded user mapping module has defined all necessary methods
         # Note parse_config() is already checked during the call to load_module
diff --git a/synapse/config/spam_checker.py b/synapse/config/spam_checker.py
index 3d067d29d..3d05abc15 100644
--- a/synapse/config/spam_checker.py
+++ b/synapse/config/spam_checker.py
@@ -33,13 +33,14 @@ class SpamCheckerConfig(Config):
             # spam checker, and thus was simply a dictionary with module
             # and config keys. Support this old behaviour by checking
             # to see if the option resolves to a dictionary
-            self.spam_checkers.append(load_module(spam_checkers))
+            self.spam_checkers.append(load_module(spam_checkers, ("spam_checker",)))
         elif isinstance(spam_checkers, list):
-            for spam_checker in spam_checkers:
+            for i, spam_checker in enumerate(spam_checkers):
+                config_path = ("spam_checker", "<item %i>" % i)
                 if not isinstance(spam_checker, dict):
-                    raise ConfigError("spam_checker syntax is incorrect")
+                    raise ConfigError("expected a mapping", config_path)
 
-                self.spam_checkers.append(load_module(spam_checker))
+                self.spam_checkers.append(load_module(spam_checker, config_path))
         else:
             raise ConfigError("spam_checker syntax is incorrect")
 
diff --git a/synapse/config/third_party_event_rules.py b/synapse/config/third_party_event_rules.py
index 10a99c792..c04e1c4e0 100644
--- a/synapse/config/third_party_event_rules.py
+++ b/synapse/config/third_party_event_rules.py
@@ -26,7 +26,9 @@ class ThirdPartyRulesConfig(Config):
 
         provider = config.get("third_party_event_rules", None)
         if provider is not None:
-            self.third_party_event_rules = load_module(provider)
+            self.third_party_event_rules = load_module(
+                provider, ("third_party_event_rules",)
+            )
 
     def generate_config_section(self, **kwargs):
         return """\
diff --git a/synapse/util/module_loader.py b/synapse/util/module_loader.py
index 94b59afb3..1ee61851e 100644
--- a/synapse/util/module_loader.py
+++ b/synapse/util/module_loader.py
@@ -15,28 +15,56 @@
 
 import importlib
 import importlib.util
+import itertools
+from typing import Any, Iterable, Tuple, Type
+
+import jsonschema
 
 from synapse.config._base import ConfigError
+from synapse.config._util import json_error_to_config_error
 
 
-def load_module(provider):
+def load_module(provider: dict, config_path: Iterable[str]) -> Tuple[Type, Any]:
     """ Loads a synapse module with its config
-    Take a dict with keys 'module' (the module name) and 'config'
-    (the config dict).
+
+    Args:
+        provider: a dict with keys 'module' (the module name) and 'config'
+           (the config dict).
+        config_path: the path within the config file. This will be used as a basis
+           for any error message.
 
     Returns
         Tuple of (provider class, parsed config object)
     """
+
+    modulename = provider.get("module")
+    if not isinstance(modulename, str):
+        raise ConfigError(
+            "expected a string", path=itertools.chain(config_path, ("module",))
+        )
+
     # We need to import the module, and then pick the class out of
     # that, so we split based on the last dot.
-    module, clz = provider["module"].rsplit(".", 1)
+    module, clz = modulename.rsplit(".", 1)
     module = importlib.import_module(module)
     provider_class = getattr(module, clz)
 
+    module_config = provider.get("config")
     try:
-        provider_config = provider_class.parse_config(provider.get("config"))
+        provider_config = provider_class.parse_config(module_config)
+    except jsonschema.ValidationError as e:
+        raise json_error_to_config_error(e, itertools.chain(config_path, ("config",)))
+    except ConfigError as e:
+        raise _wrap_config_error(
+            "Failed to parse config for module %r" % (modulename,),
+            prefix=itertools.chain(config_path, ("config",)),
+            e=e,
+        )
     except Exception as e:
-        raise ConfigError("Failed to parse config for %r: %s" % (provider["module"], e))
+        raise ConfigError(
+            "Failed to parse config for module %r" % (modulename,),
+            path=itertools.chain(config_path, ("config",)),
+        ) from e
 
     return provider_class, provider_config
 
@@ -56,3 +84,27 @@ def load_python_module(location: str):
     mod = importlib.util.module_from_spec(spec)
     spec.loader.exec_module(mod)  # type: ignore
     return mod
+
+
+def _wrap_config_error(
+    msg: str, prefix: Iterable[str], e: ConfigError
+) -> "ConfigError":
+    """Wrap a relative ConfigError with a new path
+
+    This is useful when we have a ConfigError with a relative path due to a problem
+    parsing part of the config, and we now need to set it in context.
+    """
+    path = prefix
+    if e.path:
+        path = itertools.chain(prefix, e.path)
+
+    e1 = ConfigError(msg, path)
+
+    # ideally we would set the 'cause' of the new exception to the original exception;
+    # however now that we have merged the path into our own, the stringification of
+    # e will be incorrect, so instead we create a new exception with just the "msg"
+    # part.
+
+    e1.__cause__ = Exception(e.msg)
+    e1.__cause__.__cause__ = e.__cause__
+    return e1