diff --git a/nucypher/network/server.py b/nucypher/network/server.py
index b51cbeaa1..4dfa8b8ad 100644
--- a/nucypher/network/server.py
+++ b/nucypher/network/server.py
@@ -217,7 +217,17 @@ def _make_rest_app(this_node, log: Logger) -> Flask:
         capsules_to_process = list()
         for capsule, lingo in packets:
             # raises an exception or continues
-            evaluate_conditions_for_ursula(lingo=lingo, providers=providers, context=context)
+            result, error = evaluate_conditions_for_ursula(
+                lingo=lingo, providers=providers, context=context
+            )
+            if error:
+                # error cases
+                return Response(*error)
+            elif not result:
+                # explicit condition failure
+                return Response(
+                    "Decryption conditions not satisfied", HTTPStatus.FORBIDDEN
+                )
             capsules_to_process.append((lingo, capsule))
 
         # Strip away conditions that have already been evaluated
diff --git a/nucypher/policy/conditions/_utils.py b/nucypher/policy/conditions/_utils.py
index 9d15fe4c1..f25ceb373 100644
--- a/nucypher/policy/conditions/_utils.py
+++ b/nucypher/policy/conditions/_utils.py
@@ -1,8 +1,24 @@
+"""
+ This file is part of nucypher.
+
+ nucypher is free software: you can redistribute it and/or modify
+ it under the terms of the GNU Affero General Public License as published by
+ the Free Software Foundation, either version 3 of the License, or
+ (at your option) any later version.
+
+ nucypher is distributed in the hope that it will be useful,
+ but WITHOUT ANY WARRANTY; without even the implied warranty of
+ MERCHANTABILITY or FITNESS FOR A PARTICULAR PURPOSE.  See the
+ GNU Affero General Public License for more details.
+
+ You should have received a copy of the GNU Affero General Public License
+ along with nucypher.  If not, see <https://www.gnu.org/licenses/>.
+"""
+
 import json
 from http import HTTPStatus
-from typing import Union, Type, Dict, Optional
+from typing import Dict, Optional, Tuple, Type, Union
 
-from flask import Response
 from marshmallow import Schema, post_dump
 from web3.providers import BaseProvider
 
@@ -12,6 +28,7 @@ from nucypher.policy.conditions.context import (
     InvalidContextVariableData,
     RequiredContextVariable,
 )
+from nucypher.policy.conditions.evm import RPCCondition
 from nucypher.utilities.logging import Logger
 
 _ETH = 'eth_'
@@ -48,10 +65,9 @@ def _resolve_condition_lingo(json_data) -> Union[Type['Operator'], Type['Reencry
     conditions expression framework.
     """
     # TODO: This is ugly but avoids circular imports :-|
-    from nucypher.policy.conditions.time import TimeCondition
-    from nucypher.policy.conditions.evm import ContractCondition
-    from nucypher.policy.conditions.evm import RPCCondition
+    from nucypher.policy.conditions.evm import ContractCondition, RPCCondition
     from nucypher.policy.conditions.lingo import Operator
+    from nucypher.policy.conditions.time import TimeCondition
 
     # Inspect
     method = json_data.get('method')
@@ -81,57 +97,49 @@ def _deserialize_condition_lingo(data: Union[str, Dict[str, str]]) -> Union['Ope
     return instance
 
 
-def evaluate_conditions_for_ursula(lingo: 'ConditionLingo',
-                                   providers: Optional[Dict[str, BaseProvider]] = None,
-                                   context: Optional[Dict[Union[str, int], Union[str, int]]] = None,
-                                   log: Logger = __LOGGER,
-                                   ) -> Response:
+def evaluate_conditions_for_ursula(
+    lingo: "ConditionLingo",
+    providers: Optional[Dict[str, BaseProvider]] = None,
+    context: Optional[Dict[Union[str, int], Union[str, int]]] = None,
+    log: Logger = __LOGGER,
+) -> Tuple[bool, Optional[Tuple[str, HTTPStatus]]]:
 
     # avoid using a mutable defaults and support federated mode
     context = context or dict()
     providers = providers or dict()
-
+    result, error = False, None
     if lingo is not None:
         # TODO: Evaluate all conditions even if one fails and report the result
         try:
             log.info(f'Evaluating access conditions {lingo.id}')
-            _results = lingo.eval(providers=providers, **context)
+            result = lingo.eval(providers=providers, **context)
         except ReencryptionCondition.InvalidCondition as e:
             message = f"Incorrect value provided for condition: {e}"
             error = (message, HTTPStatus.BAD_REQUEST)
-            log.info(message)
-            return Response(message, status=error[1])
         except RequiredContextVariable as e:
             message = f"Missing required inputs: {e}"
             # TODO: be more specific and name the missing inputs, etc
             error = (message, HTTPStatus.BAD_REQUEST)
-            log.info(message)
-            return Response(message, status=error[1])
         except InvalidContextVariableData as e:
             message = f"Invalid data provided for context variable: {e}"
             error = (message, HTTPStatus.BAD_REQUEST)
-            log.info(message)
-            return Response(message, status=error[1])
         except ContextVariableVerificationFailed as e:
             message = f"Context variable data could not be verified: {e}"
             error = (message, HTTPStatus.FORBIDDEN)
-            log.info(message)
-            return Response(message, status=error[1])
+        except RPCCondition.NoConnectionToChain as e:
+            message = f"Node does not have a connection to chain ID {e.chain}: {e}"
+            error = (message, HTTPStatus.NOT_IMPLEMENTED)
         except ReencryptionCondition.ConditionEvaluationFailed as e:
             message = f"Decryption condition not evaluated: {e}"
             error = (message, HTTPStatus.BAD_REQUEST)
-            log.info(message)
-            return Response(message, status=error[1])
-        except lingo.Failed as e:
-            # TODO: Better error reporting
-            message = f"Decryption conditions not satisfied: {e}"
-            error = (message, HTTPStatus.FORBIDDEN)
-            log.info(message)
-            return Response(message, status=error[1])
         except Exception as e:
             # TODO: Unsure why we ended up here
             message = f"Unexpected exception while evaluating " \
                       f"decryption condition ({e.__class__.__name__}): {e}"
             error = (message, HTTPStatus.INTERNAL_SERVER_ERROR)
             log.warn(message)
-            return Response(message, status=error[1])
+
+    if error:
+        log.info(error[0])
+
+    return result, error
diff --git a/nucypher/policy/conditions/evm.py b/nucypher/policy/conditions/evm.py
index 1d9c271da..d4e9b349a 100644
--- a/nucypher/policy/conditions/evm.py
+++ b/nucypher/policy/conditions/evm.py
@@ -16,7 +16,7 @@
 """
 
 import re
-from typing import Any, List, Optional, Tuple, Dict
+from typing import Any, Dict, List, Optional, Tuple
 
 from eth_typing import ChecksumAddress
 from eth_utils import to_checksum_address
@@ -31,7 +31,6 @@ from nucypher.policy.conditions.base import ReencryptionCondition
 from nucypher.policy.conditions.context import get_context_value, is_context_variable
 from nucypher.policy.conditions.lingo import ReturnValueTest
 
-
 # Permitted blockchains for condition evaluation
 _CONDITION_CHAINS = (
     1,     # ethereum/mainnet
@@ -113,6 +112,13 @@ class RPCCondition(ReencryptionCondition):
     class RPCExecutionFailed(ReencryptionCondition.ConditionEvaluationFailed):
         """Raised when an exception is raised from an RPC call."""
 
+    class NoConnectionToChain(RuntimeError):
+        """Raised when a node does not have an associated provider for a chain."""
+
+        def __init__(self, chain: int, *args, **kwargs):
+            self.chain = chain
+            super().__init__(*args, **kwargs)
+
     class Schema(CamelCaseSchema):
         name = fields.Str(required=False)
         chain = fields.Int(required=True)
@@ -163,9 +169,10 @@ class RPCCondition(ReencryptionCondition):
         try:
             provider = providers[self.chain]
         except KeyError:
-            # TODO Use a custom exception class, and catch bubble it up to include info about the node
-            # QUESTION Are nodes required to provide connections to all providers?
-            raise Exception(f'This node does not have a connection to chain {self.chain}')
+            raise self.NoConnectionToChain(
+                chain=self.chain,
+                message=f"This node does not have a connection to chain ID {self.chain}",
+            )
 
         # Instantiate a local web3 instance
         self.w3 = Web3(provider)
diff --git a/nucypher/policy/conditions/lingo.py b/nucypher/policy/conditions/lingo.py
index 5b05aac64..aeac49d29 100644
--- a/nucypher/policy/conditions/lingo.py
+++ b/nucypher/policy/conditions/lingo.py
@@ -21,7 +21,7 @@ import base64
 import json
 import operator as pyoperator
 from hashlib import md5
-from typing import Any, Dict, List, Union, Iterator
+from typing import Any, Dict, Iterator, List, Union
 
 from marshmallow import fields, post_load
 
@@ -191,6 +191,9 @@ class ConditionLingo:
         data = self.to_json().encode()
         return data
 
+    def __repr__(self):
+        return f"{self.__class__.__name__} (id={self.id} | size={len(bytes(self))})"
+
     def __eval(self, eval_string: str):
         # TODO: Additional protection and/or sanitation here
         result = eval(eval_string)
@@ -214,9 +217,7 @@ class ConditionLingo:
         # [True, <Operator>, False] -> 'True or False'
         eval_string = ' '.join(str(e) for e in data)
         result = self.__eval(eval_string=eval_string)
-        if not result:
-            raise self.Failed
-        return True
+        return result
 
 
 OR = Operator('or')