diff --git a/CHANGELOG.md b/CHANGELOG.md
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -1,5 +1,11 @@
 # Changelog for `cuddle`
 
+## 1.5.0.0
+
+* Fix custom validators not running when reached via type-specific validators
+* Replace `TerminalRule (Maybe ControlInfo)` with `TerminalRule` and a new `ControlTrace` constructor
+* Fix `InvalidTag` trace showing the bad tag as the expected value
+
 ## 1.4.0.0
 
 * Changed `generateFromName` to return a `CBORGen` instead of `AntiGen`
diff --git a/cuddle.cabal b/cuddle.cabal
--- a/cuddle.cabal
+++ b/cuddle.cabal
@@ -1,6 +1,6 @@
 cabal-version: 3.4
 name: cuddle
-version: 1.4.0.0
+version: 1.5.0.0
 synopsis: CDDL Generator and test utilities
 description:
   Cuddle is a library for generating and manipulating [CDDL](https://datatracker.ietf.org/doc/html/rfc8610).
diff --git a/src/Codec/CBOR/Cuddle/CBOR/Gen.hs b/src/Codec/CBOR/Cuddle/CBOR/Gen.hs
--- a/src/Codec/CBOR/Cuddle/CBOR/Gen.hs
+++ b/src/Codec/CBOR/Cuddle/CBOR/Gen.hs
@@ -402,7 +402,10 @@
     genNodes !i !m (n : ns) =
       let
         ann = withAntiGen (withAnnotation (T.pack $ show i))
-        cont x y = scale (\s -> max 0 (s - 1)) $ genNodes (i + 1) x y
+        -- A term was produced, advance the index
+        next x y = scale (\s -> max 0 (s - 1)) $ genNodes (i + 1) x y
+        -- No term was produced, keep the index
+        same x y = scale (\s -> max 0 (s - 1)) $ genNodes i x y
         optGenKV kNode vNode = sized $ \sz ->
           frequency [(100, pure Nothing), (max 0 sz, ann $ tryGenKV 10 m kNode vNode)]
        in
@@ -410,19 +413,19 @@
           KV kNode vNode _ -> do
             mKV <- ann $ tryGenKV 100 m kNode vNode
             case mKV of
-              Just (k, v) -> cont (Map.insert k v m) ns
+              Just (k, v) -> next (Map.insert k v m) ns
               Nothing -> pure Nothing
           Occur kv@(KV kNode vNode _) oi -> case oi of
             OIOptional -> do
               mt <- optGenKV kNode vNode
               case mt of
-                Just (k, v) -> cont (Map.insert k v m) ns
-                Nothing -> cont m ns
+                Just (k, v) -> next (Map.insert k v m) ns
+                Nothing -> same m ns
             OIZeroOrMore -> do
               mt <- optGenKV kNode vNode
               case mt of
-                Just (k, v) -> cont (Map.insert k v m) (n : ns)
-                Nothing -> cont m ns
+                Just (k, v) -> next (Map.insert k v m) (n : ns)
+                Nothing -> same m ns
             OIOneOrMore -> genNodes i m (kv : Occur kv OIZeroOrMore : ns)
             OIBounded mlb mub -> do
               let
@@ -432,12 +435,12 @@
                 newHigh = clampedPred <$> mub
                 res
                   | maybe False (> 0) mlb = genNodes i m (kv : Occur kv (OIBounded newLow newHigh) : ns)
-                  | maybe False (< 1) mub = genNodes i m ns
+                  | maybe False (< 1) mub = same m ns
                   | otherwise = do
                       mt <- optGenKV kNode vNode
                       case mt of
-                        Just (k, v) -> cont (Map.insert k v m) (Occur kv (OIBounded newLow newHigh) : ns)
-                        Nothing -> genNodes i m ns
+                        Just (k, v) -> next (Map.insert k v m) (Occur kv (OIBounded newLow newHigh) : ns)
+                        Nothing -> same m ns
               res
           node -> error $ "Unexpected node: " <> showSimple node
   mItems <- genNodes 0 Map.empty $ sortOn (Down . elemsNeeded) nodes
diff --git a/src/Codec/CBOR/Cuddle/CBOR/Validator.hs b/src/Codec/CBOR/Cuddle/CBOR/Validator.hs
--- a/src/Codec/CBOR/Cuddle/CBOR/Validator.hs
+++ b/src/Codec/CBOR/Cuddle/CBOR/Validator.hs
@@ -22,7 +22,6 @@
   isValid,
   mapTrace,
   showSimple,
-  showValidationTrace,
  )
 import Codec.CBOR.Cuddle.CDDL hiding (CDDL, Group, Rule)
 import Codec.CBOR.Cuddle.CDDL.CBORGenerator (CBORValidator (..), CustomValidatorResult (..))
@@ -79,10 +78,8 @@
 validateTerm cddl term rule
   | CTreeE (VRuleRef n) <- rule =
       dereferenceAndValidate cddl n (validateTerm cddl term)
-  | CTreeE (VValidator (CBORValidator validator) _) <- rule =
-      case validator term of
-        CustomValidatorSuccess -> evidence CustomSuccess
-        CustomValidatorFailure err -> evidence $ CustomFailure err
+  | CTreeE (VValidator v _) <- rule =
+      runCustomValidator term v
   | otherwise =
       case term of
         TInt i -> validateInteger cddl (fromIntegral i) rule
@@ -104,8 +101,16 @@
         TDouble d -> validateDouble cddl d rule
 
 terminal :: CTree ValidatorStage -> Evidenced ValidationTrace
-terminal = evidence . TerminalRule Nothing . mapIndex
+terminal = evidence . TerminalRule . mapIndex
 
+-- | Run a custom validator on a term. This is used by type-specific validators
+-- when they encounter a 'VValidator' node after dereferencing a rule reference.
+runCustomValidator :: Term -> CBORValidator -> Evidenced ValidationTrace
+runCustomValidator term (CBORValidator validator) =
+  case validator term of
+    CustomValidatorSuccess -> evidence CustomSuccess
+    CustomValidatorFailure err -> evidence $ CustomFailure err
+
 unapplicable :: CTree ValidatorStage -> Evidenced ValidationTrace
 unapplicable = evidence . UnapplicableRule . mapIndex
 
@@ -132,6 +137,7 @@
 validateInteger cddl i rule =
   case rule of
     CTreeE (VRuleRef n) -> dereferenceAndValidate cddl n $ validateInteger cddl i
+    CTreeE (VValidator v _) -> runCustomValidator (TInteger i) v
     -- echo "C24101" | xxd -r -p - example.cbor
     -- echo "foo = int" > a.cddl
     -- cddl a.cddl validate example.cbor
@@ -301,6 +307,7 @@
   CTree ValidatorStage ->
   Evidenced ValidationTrace
 validateHalf cddl f (CTreeE (VRuleRef n)) = dereferenceAndValidate cddl n $ validateHalf cddl f
+validateHalf _ f (CTreeE (VValidator v _)) = runCustomValidator (THalf f) v
 validateHalf cddl f rule =
   case rule of
     -- a = any
@@ -351,6 +358,7 @@
   Evidenced ValidationTrace
 validateFloat cddl f (CTreeE (VRuleRef n)) =
   dereferenceAndValidate cddl n $ validateFloat cddl f
+validateFloat _ f (CTreeE (VValidator v _)) = runCustomValidator (TFloat f) v
 validateFloat cddl f rule =
   case rule of
     -- a = any
@@ -412,6 +420,7 @@
   Evidenced ValidationTrace
 validateDouble cddl f (CTreeE (VRuleRef n)) =
   dereferenceAndValidate cddl n $ validateDouble cddl f
+validateDouble _ f (CTreeE (VValidator v _)) = runCustomValidator (TDouble f) v
 validateDouble cddl f rule =
   case rule of
     -- a = any
@@ -481,6 +490,7 @@
   Evidenced ValidationTrace
 validateBool cddl b (CTreeE (VRuleRef n)) =
   dereferenceAndValidate cddl n $ validateBool cddl b
+validateBool _ b (CTreeE (VValidator v _)) = runCustomValidator (TBool b) v
 validateBool cddl b rule =
   case rule of
     -- a = any
@@ -526,6 +536,7 @@
   Evidenced ValidationTrace
 validateSimple cddl i (CTreeE (VRuleRef n)) =
   dereferenceAndValidate cddl n $ validateSimple cddl i
+validateSimple _ i (CTreeE (VValidator v _)) = runCustomValidator (TSimple i) v
 validateSimple cddl 23 rule =
   case rule of
     -- a = any
@@ -544,6 +555,7 @@
 validateNull :: CTreeRoot ValidatorStage -> CTree ValidatorStage -> Evidenced ValidationTrace
 validateNull cddl (CTreeE (VRuleRef n)) =
   dereferenceAndValidate cddl n $ validateNull cddl
+validateNull _ (CTreeE (VValidator v _)) = runCustomValidator TNull v
 validateNull cddl rule =
   case rule of
     -- a = any
@@ -561,6 +573,7 @@
   CTreeRoot ValidatorStage -> BS.ByteString -> CTree ValidatorStage -> Evidenced ValidationTrace
 validateBytes cddl bs (CTreeE (VRuleRef n)) =
   dereferenceAndValidate cddl n $ validateBytes cddl bs
+validateBytes _ bs (CTreeE (VValidator v _)) = runCustomValidator (TBytes bs) v
 validateBytes cddl bs rule =
   case rule of
     -- a = any
@@ -646,6 +659,7 @@
   Evidenced ValidationTrace
 validateText cddl txt (CTreeE (VRuleRef n)) =
   dereferenceAndValidate cddl n $ validateText cddl txt
+validateText _ txt (CTreeE (VValidator v _)) = runCustomValidator (TString txt) v
 validateText cddl txt rule =
   case rule of
     -- a = any
@@ -704,6 +718,7 @@
   CTreeRoot ValidatorStage -> Word64 -> Term -> CTree ValidatorStage -> Evidenced ValidationTrace
 validateTagged cddl tag term (CTreeE (VRuleRef n)) =
   dereferenceAndValidate cddl n $ validateTagged cddl tag term
+validateTagged _ tag term (CTreeE (VValidator v _)) = runCustomValidator (TTagged tag term) v
 validateTagged cddl tag term rule =
   case rule of
     Postlude PTAny -> terminal rule
@@ -711,7 +726,7 @@
       -- If the tag does not match, this is a direct fail
       if tag == tag'
         then mapTrace (TagTrace tag) $ validateTerm cddl term rule'
-        else evidence $ InvalidTag tag
+        else evidence $ InvalidTag tag' tag
     Choice opts -> validateChoice (validateTagged cddl tag term) opts
     _ -> unapplicable rule
 
@@ -757,6 +772,7 @@
   Evidenced ValidationTrace
 validateList cddl terms (CTreeE (VRuleRef n)) =
   dereferenceAndValidate cddl n $ validateList cddl terms
+validateList _ terms (CTreeE (VValidator v _)) = runCustomValidator (TList terms) v
 validateList cddl terms rule =
   case rule of
     Postlude PTAny -> terminal rule
@@ -842,6 +858,7 @@
   Evidenced ValidationTrace
 validateMap cddl terms (CTreeE (VRuleRef n)) =
   dereferenceAndValidate cddl n $ validateMap cddl terms
+validateMap _ terms (CTreeE (VValidator v _)) = runCustomValidator (TMap terms) v
 validateMap cddl terms rule =
   case rule of
     Postlude PTAny -> terminal rule
@@ -952,13 +969,11 @@
 ctrlDispatch v Within tgt ctrl _ = ctrlAnd v tgt ctrl
 ctrlDispatch v op tgt ctrl vctrl =
   case v tgt of
-    Evidenced SValid (TerminalRule _ res)
+    Evidenced SValid trc
       | vctrl op ctrl ->
-          evidence $ TerminalRule (Just (ControlInfo op (mapIndex ctrl))) res
+          evidence $ ControlTrace (ControlInfo op (mapIndex ctrl)) trc
       | otherwise ->
           evidence $ UnsatisfiedControl op (mapIndex ctrl)
-    Evidenced SValid trc ->
-      error $ "Unexpected trace:\n\t" <> showValidationTrace trc
     err -> err
 
 --------------------------------------------------------------------------------
diff --git a/src/Codec/CBOR/Cuddle/CBOR/Validator/Trace.hs b/src/Codec/CBOR/Cuddle/CBOR/Validator/Trace.hs
--- a/src/Codec/CBOR/Cuddle/CBOR/Validator/Trace.hs
+++ b/src/Codec/CBOR/Cuddle/CBOR/Validator/Trace.hs
@@ -170,7 +170,8 @@
 
 data ValidationTrace (v :: Validity) where
   UnapplicableRule :: CTree ValidatorStageSimple -> ValidationTrace IsInvalid
-  TerminalRule :: Maybe ControlInfo -> CTree ValidatorStageSimple -> ValidationTrace IsValid
+  TerminalRule :: CTree ValidatorStageSimple -> ValidationTrace IsValid
+  ControlTrace :: ControlInfo -> ValidationTrace IsValid -> ValidationTrace IsValid
   ReferenceRule :: Name -> ValidationTrace v -> ValidationTrace v
   CustomFailure :: Text -> ValidationTrace IsInvalid
   CustomSuccess :: ValidationTrace IsValid
@@ -179,7 +180,7 @@
   ListTrace :: ListValidationTrace v -> ValidationTrace v
   MapTrace :: MapValidationTrace v -> ValidationTrace v
   TagTrace :: Word64 -> ValidationTrace v -> ValidationTrace v
-  InvalidTag :: Word64 -> ValidationTrace IsInvalid
+  InvalidTag :: Word64 -> Word64 -> ValidationTrace IsInvalid
 
 deriving instance Show (ValidationTrace v)
 
@@ -283,6 +284,7 @@
   traceValidity = \case
     CustomSuccess {} -> SValid
     TerminalRule {} -> SValid
+    ControlTrace {} -> SValid
     ChoiceBranch {} -> SValid
     UnapplicableRule {} -> SInvalid
     CustomFailure {} -> SInvalid
@@ -296,6 +298,7 @@
   measureProgress = \case
     TerminalRule {} -> Progress 1 0
     CustomSuccess -> Progress 1 0
+    ControlTrace _ x -> measureProgress x
     ChoiceBranch _ x -> measureProgress x
     UnapplicableRule {} -> mempty
     CustomFailure {} -> mempty
@@ -473,15 +476,12 @@
 prettyValidationTrace :: TraceOptions -> ValidationTrace v -> Doc AnsiStyle
 prettyValidationTrace opts = \case
   UnapplicableRule x -> annotate (color Red) $ vsep ["failed to apply: ", indent 2 $ pretty x]
-  TerminalRule mCi x -> case mCi of
-    Just ci ->
-      vsep
-        [ appMsg
-        , nestContainer $ "ctrl:" <+> annotate (color Yellow) ("." <> pretty ci)
-        ]
-    Nothing -> appMsg
-    where
-      appMsg = "app: " <> annotate (color Green) (pretty x)
+  TerminalRule x -> "app: " <> annotate (color Green) (pretty x)
+  ControlTrace ci x ->
+    vsep
+      [ prettyValidationTrace opts x
+      , nestContainer $ "ctrl:" <+> annotate (color Yellow) ("." <> pretty ci)
+      ]
   ChoiceBranch i c ->
     vsep
       [ "choice (idx: " <> pretty i <> ")"
@@ -515,8 +515,8 @@
       [ "tag:" <+> annotate (color Green) ("#6." <> pretty t)
       , nestContainer $ prettyValidationTrace opts x
       ]
-  InvalidTag t ->
-    "expected tag #6." <> pretty t
+  InvalidTag expected actual ->
+    "expected tag #6." <> pretty expected <> ", got #6." <> pretty actual
 
 showValidationTrace :: ValidationTrace v -> String
 showValidationTrace =
diff --git a/test/Test/Codec/CBOR/Cuddle/CDDL/Validator.hs b/test/Test/Codec/CBOR/Cuddle/CDDL/Validator.hs
--- a/test/Test/Codec/CBOR/Cuddle/CDDL/Validator.hs
+++ b/test/Test/Codec/CBOR/Cuddle/CDDL/Validator.hs
@@ -39,6 +39,7 @@
   withValidator,
   (=:=),
  )
+import Codec.CBOR.Cuddle.Huddle qualified as H
 import Codec.CBOR.Cuddle.IndexMappable (mapCDDLDropExt, mapIndex)
 import Codec.CBOR.Cuddle.Parser (pCDDL)
 import Codec.CBOR.Pretty (prettyHexEnc)
@@ -373,6 +374,17 @@
               [ HIRule ruleA
               , HIRule $ "b" =:= arr [a ruleA]
               ]
+        pure . expectValid $ validateHuddle huddle "b" arrTerm
+      prop "Validates with custom validator in a choice within a group" $ do
+        bs <- BS.pack <$> listOf1 arbitrary
+        let
+          ruleA = withValidator bytesValidator $ "a" =:= VText
+          huddle =
+            collectFrom
+              [ HIRule ruleA
+              , HIRule $ "b" =:= arr [0, a (ruleA H./ VNil)]
+              ]
+        arrTerm <- genArrayTerm [TInt 0, TBytes bs]
         pure . expectValid $ validateHuddle huddle "b" arrTerm
     describe "Negative" $ do
       prop "Fails if term is valid against the Huddle, but not the custom validator" $ do