diff --git a/src/compiler/checker.ts b/src/compiler/checker.ts
index 8547fc7e1760e..0bfbb5021abe0 100644
--- a/src/compiler/checker.ts
+++ b/src/compiler/checker.ts
@@ -8885,6 +8885,16 @@ namespace ts {
                 return false;
             }
 
+            function reportElaboratedRelationError(headMessage: DiagnosticMessage | undefined, source: Type, target: Type) {
+                if (source.flags & TypeFlags.Object && target.flags & TypeFlags.Primitive) {
+                    tryElaborateErrorsForPrimitivesAndObjects(source, target);
+                }
+                else if (source.symbol && source.flags & TypeFlags.Object && globalObjectType === source) {
+                    reportError(Diagnostics.The_Object_type_is_assignable_to_very_few_other_types_Did_you_mean_to_use_the_any_type_instead);
+                }
+                reportRelationError(headMessage, source, target);
+            }
+
             /**
              * Compare two types and return
              * * Ternary.True if they are related with no assumptions,
@@ -8899,20 +8909,36 @@ namespace ts {
                     target = (<LiteralType>target).regularType;
                 }
                 // both types are the same - covers 'they are the same primitive type or both are Any' or the same type parameter cases
-                if (source === target) return Ternary.True;
+                if (source === target || relation !== identityRelation && isSimpleTypeRelatedTo(source, target, relation, reportErrors ? reportError : undefined)) {
+                    return Ternary.True;
+                }
 
-                if (relation === identityRelation) {
-                    return isIdenticalTo(source, target);
+                const id = getRelationKey(source, target, relation);
+                const related = relation.get(id);
+                if (related !== undefined) {
+                    // If we need to report errors, and the result is RelationComparisonResult.Failed, then we need
+                    // to redo our work to generate an error message. Otherwise, we can just return the cached result.
+                    if (!reportErrors || related !== RelationComparisonResult.Failed) {
+                        if (reportErrors && related !== RelationComparisonResult.Succeeded) {
+                            reportElaboratedRelationError(headMessage, source, target);
+                        }
+                        return related === RelationComparisonResult.Succeeded ? Ternary.True : Ternary.False;
+                    }
+                    if (reportErrors && related === RelationComparisonResult.Failed) {
+                        relation.set(id, RelationComparisonResult.FailedAndReported);
+                    }
                 }
 
-                if (isSimpleTypeRelatedTo(source, target, relation, reportErrors ? reportError : undefined)) return Ternary.True;
+                if (relation === identityRelation) {
+                    return cacheResult(isIdenticalTo(source, target, id), id, /*reportErrors*/ false);
+                }
 
                 if (getObjectFlags(source) & ObjectFlags.ObjectLiteral && source.flags & TypeFlags.FreshLiteral) {
                     if (hasExcessProperties(<FreshObjectLiteralType>source, target, reportErrors)) {
                         if (reportErrors) {
                             reportRelationError(headMessage, source, target);
                         }
-                        return Ternary.False;
+                        return cacheResult(Ternary.False, id, reportErrors);
                     }
                     // Above we check for excess properties with respect to the entire target type. When union
                     // and intersection types are further deconstructed on the target side, we don't want to
@@ -8944,6 +8970,7 @@ namespace ts {
                             reportError(Diagnostics.Type_0_has_no_properties_in_common_with_type_1, typeToString(source), typeToString(target));
                         }
                     }
+                    // Intentionally not cached, so common property errors are repeated
                     return Ternary.False;
                 }
 
@@ -8985,7 +9012,7 @@ namespace ts {
                         result = someTypeRelatedToType(<IntersectionType>source, target, /*reportErrors*/ false);
                     }
                     if (!result && (source.flags & TypeFlags.StructuredOrTypeVariable || target.flags & TypeFlags.StructuredOrTypeVariable)) {
-                        if (result = recursiveTypeRelatedTo(source, target, reportErrors)) {
+                        if (result = recursiveTypeRelatedTo(source, target, id, reportErrors)) {
                             errorInfo = saveErrorInfo;
                         }
                     }
@@ -8994,21 +9021,23 @@ namespace ts {
                 isIntersectionConstituent = saveIsIntersectionConstituent;
 
                 if (!result && reportErrors) {
-                    if (source.flags & TypeFlags.Object && target.flags & TypeFlags.Primitive) {
-                        tryElaborateErrorsForPrimitivesAndObjects(source, target);
-                    }
-                    else if (source.symbol && source.flags & TypeFlags.Object && globalObjectType === source) {
-                        reportError(Diagnostics.The_Object_type_is_assignable_to_very_few_other_types_Did_you_mean_to_use_the_any_type_instead);
-                    }
-                    reportRelationError(headMessage, source, target);
+                    reportElaboratedRelationError(headMessage, source, target);
+                }
+
+                return cacheResult(result, id, reportErrors);
+            }
+
+            function cacheResult(result: Ternary, comparisonId: string, reportErrors?: boolean) {
+                if (!relation.has(comparisonId) && result !== Ternary.Maybe) {
+                    relation.set(comparisonId, result ? RelationComparisonResult.Succeeded : reportErrors ? RelationComparisonResult.FailedAndReported : RelationComparisonResult.Failed);
                 }
                 return result;
             }
 
-            function isIdenticalTo(source: Type, target: Type): Ternary {
+            function isIdenticalTo(source: Type, target: Type, id: string): Ternary {
                 let result: Ternary;
                 if (source.flags & TypeFlags.Object && target.flags & TypeFlags.Object) {
-                    return recursiveTypeRelatedTo(source, target, /*reportErrors*/ false);
+                    return recursiveTypeRelatedTo(source, target, id, /*reportErrors*/ false);
                 }
                 if (source.flags & TypeFlags.Union && target.flags & TypeFlags.Union ||
                     source.flags & TypeFlags.Intersection && target.flags & TypeFlags.Intersection) {
@@ -9184,22 +9213,10 @@ namespace ts {
             // Third, check if both types are part of deeply nested chains of generic type instantiations and if so assume the types are
             // equal and infinitely expanding. Fourth, if we have reached a depth of 100 nested comparisons, assume we have runaway recursion
             // and issue an error. Otherwise, actually compare the structure of the two types.
-            function recursiveTypeRelatedTo(source: Type, target: Type, reportErrors: boolean): Ternary {
+            function recursiveTypeRelatedTo(source: Type, target: Type, id: string, reportErrors: boolean): Ternary {
                 if (overflow) {
                     return Ternary.False;
                 }
-                const id = getRelationKey(source, target, relation);
-                const related = relation.get(id);
-                if (related !== undefined) {
-                    if (reportErrors && related === RelationComparisonResult.Failed) {
-                        // We are elaborating errors and the cached result is an unreported failure. Record the result as a reported
-                        // failure and continue computing the relation such that errors get reported.
-                        relation.set(id, RelationComparisonResult.FailedAndReported);
-                    }
-                    else {
-                        return related === RelationComparisonResult.Succeeded ? Ternary.True : Ternary.False;
-                    }
-                }
                 if (!maybeKeys) {
                     maybeKeys = [];
                     sourceStack = [];
@@ -9239,9 +9256,6 @@ namespace ts {
                     }
                 }
                 else {
-                    // A false result goes straight into global cache (when something is false under
-                    // assumptions it will also be false without assumptions)
-                    relation.set(id, reportErrors ? RelationComparisonResult.FailedAndReported : RelationComparisonResult.Failed);
                     maybeCount = maybeStart;
                 }
                 return result;
diff --git a/tests/baselines/reference/arityAndOrderCompatibility01.errors.txt b/tests/baselines/reference/arityAndOrderCompatibility01.errors.txt
index 5a367a4122fe0..970372ca0c1c6 100644
--- a/tests/baselines/reference/arityAndOrderCompatibility01.errors.txt
+++ b/tests/baselines/reference/arityAndOrderCompatibility01.errors.txt
@@ -31,7 +31,6 @@ tests/cases/conformance/types/tuple/arityAndOrderCompatibility01.ts(26,5): error
   Types of property 'pop' are incompatible.
     Type '() => string | number' is not assignable to type '() => string'.
       Type 'string | number' is not assignable to type 'string'.
-        Type 'number' is not assignable to type 'string'.
 tests/cases/conformance/types/tuple/arityAndOrderCompatibility01.ts(27,5): error TS2322: Type '{ 0: string; 1: number; }' is not assignable to type '[string]'.
   Property 'length' is missing in type '{ 0: string; 1: number; }'.
 tests/cases/conformance/types/tuple/arityAndOrderCompatibility01.ts(28,5): error TS2322: Type '[string, number]' is not assignable to type '[number, string]'.
@@ -118,7 +117,6 @@ tests/cases/conformance/types/tuple/arityAndOrderCompatibility01.ts(30,5): error
 !!! error TS2322:   Types of property 'pop' are incompatible.
 !!! error TS2322:     Type '() => string | number' is not assignable to type '() => string'.
 !!! error TS2322:       Type 'string | number' is not assignable to type 'string'.
-!!! error TS2322:         Type 'number' is not assignable to type 'string'.
     var m3: [string] = z;
         ~~
 !!! error TS2322: Type '{ 0: string; 1: number; }' is not assignable to type '[string]'.
diff --git a/tests/baselines/reference/callWithSpread2.errors.txt b/tests/baselines/reference/callWithSpread2.errors.txt
index 89617ab6074c3..44bb2bb8f2f19 100644
--- a/tests/baselines/reference/callWithSpread2.errors.txt
+++ b/tests/baselines/reference/callWithSpread2.errors.txt
@@ -1,15 +1,10 @@
 tests/cases/conformance/expressions/functionCalls/callWithSpread2.ts(30,5): error TS2345: Argument of type 'string | number' is not assignable to parameter of type 'number'.
   Type 'string' is not assignable to type 'number'.
 tests/cases/conformance/expressions/functionCalls/callWithSpread2.ts(31,5): error TS2345: Argument of type 'string | number' is not assignable to parameter of type 'number'.
-  Type 'string' is not assignable to type 'number'.
 tests/cases/conformance/expressions/functionCalls/callWithSpread2.ts(32,13): error TS2345: Argument of type 'string | number' is not assignable to parameter of type 'number'.
-  Type 'string' is not assignable to type 'number'.
 tests/cases/conformance/expressions/functionCalls/callWithSpread2.ts(33,13): error TS2345: Argument of type 'string | number' is not assignable to parameter of type 'number'.
-  Type 'string' is not assignable to type 'number'.
 tests/cases/conformance/expressions/functionCalls/callWithSpread2.ts(34,11): error TS2345: Argument of type 'string | number' is not assignable to parameter of type 'number'.
-  Type 'string' is not assignable to type 'number'.
 tests/cases/conformance/expressions/functionCalls/callWithSpread2.ts(35,11): error TS2345: Argument of type 'string | number' is not assignable to parameter of type 'number'.
-  Type 'string' is not assignable to type 'number'.
 tests/cases/conformance/expressions/functionCalls/callWithSpread2.ts(36,1): error TS2556: Expected 1-3 arguments, but got a minimum of 0.
 tests/cases/conformance/expressions/functionCalls/callWithSpread2.ts(37,1): error TS2556: Expected 1-3 arguments, but got a minimum of 0.
 tests/cases/conformance/expressions/functionCalls/callWithSpread2.ts(38,1): error TS2556: Expected 1-3 arguments, but got a minimum of 0.
@@ -52,23 +47,18 @@ tests/cases/conformance/expressions/functionCalls/callWithSpread2.ts(38,1): erro
     all(...tuple)
         ~~~~~~~~
 !!! error TS2345: Argument of type 'string | number' is not assignable to parameter of type 'number'.
-!!! error TS2345:   Type 'string' is not assignable to type 'number'.
     prefix("b", ...mixed)
                 ~~~~~~~~
 !!! error TS2345: Argument of type 'string | number' is not assignable to parameter of type 'number'.
-!!! error TS2345:   Type 'string' is not assignable to type 'number'.
     prefix("c", ...tuple)
                 ~~~~~~~~
 !!! error TS2345: Argument of type 'string | number' is not assignable to parameter of type 'number'.
-!!! error TS2345:   Type 'string' is not assignable to type 'number'.
     rest("e", ...mixed)
               ~~~~~~~~
 !!! error TS2345: Argument of type 'string | number' is not assignable to parameter of type 'number'.
-!!! error TS2345:   Type 'string' is not assignable to type 'number'.
     rest("f", ...tuple)
               ~~~~~~~~
 !!! error TS2345: Argument of type 'string | number' is not assignable to parameter of type 'number'.
-!!! error TS2345:   Type 'string' is not assignable to type 'number'.
     prefix(...ns) // required parameters are required
     ~~~~~~~~~~~~~
 !!! error TS2556: Expected 1-3 arguments, but got a minimum of 0.
diff --git a/tests/baselines/reference/checkJsxChildrenProperty7.errors.txt b/tests/baselines/reference/checkJsxChildrenProperty7.errors.txt
index ea31d008b2f54..5354d1fbb803c 100644
--- a/tests/baselines/reference/checkJsxChildrenProperty7.errors.txt
+++ b/tests/baselines/reference/checkJsxChildrenProperty7.errors.txt
@@ -9,12 +9,10 @@ tests/cases/conformance/jsx/file.tsx(25,16): error TS2322: Type '{ a: 10; b: "hi
   Type '{ a: 10; b: "hi"; children: (string | Element)[]; }' is not assignable to type 'Prop'.
     Types of property 'children' are incompatible.
       Type '(string | Element)[]' is not assignable to type 'Element | Element[]'.
-        Type '(string | Element)[]' is not assignable to type 'Element[]'.
 tests/cases/conformance/jsx/file.tsx(27,16): error TS2322: Type '{ a: 10; b: "hi"; children: (string | Element)[]; }' is not assignable to type 'IntrinsicAttributes & Prop'.
   Type '{ a: 10; b: "hi"; children: (string | Element)[]; }' is not assignable to type 'Prop'.
     Types of property 'children' are incompatible.
       Type '(string | Element)[]' is not assignable to type 'Element | Element[]'.
-        Type '(string | Element)[]' is not assignable to type 'Element[]'.
 
 
 ==== tests/cases/conformance/jsx/file.tsx (3 errors) ====
@@ -56,7 +54,6 @@ tests/cases/conformance/jsx/file.tsx(27,16): error TS2322: Type '{ a: 10; b: "hi
 !!! error TS2322:   Type '{ a: 10; b: "hi"; children: (string | Element)[]; }' is not assignable to type 'Prop'.
 !!! error TS2322:     Types of property 'children' are incompatible.
 !!! error TS2322:       Type '(string | Element)[]' is not assignable to type 'Element | Element[]'.
-!!! error TS2322:         Type '(string | Element)[]' is not assignable to type 'Element[]'.
         <AnotherButton />  </Comp>;
     let k3 = <Comp a={10} b="hi">    <Button />
                    ~~~~~~~~~~~~~
@@ -64,5 +61,4 @@ tests/cases/conformance/jsx/file.tsx(27,16): error TS2322: Type '{ a: 10; b: "hi
 !!! error TS2322:   Type '{ a: 10; b: "hi"; children: (string | Element)[]; }' is not assignable to type 'Prop'.
 !!! error TS2322:     Types of property 'children' are incompatible.
 !!! error TS2322:       Type '(string | Element)[]' is not assignable to type 'Element | Element[]'.
-!!! error TS2322:         Type '(string | Element)[]' is not assignable to type 'Element[]'.
         <AnotherButton /></Comp>;
\ No newline at end of file
diff --git a/tests/baselines/reference/contextualTypeWithTuple.errors.txt b/tests/baselines/reference/contextualTypeWithTuple.errors.txt
index a488d8c764829..be9286b4a8302 100644
--- a/tests/baselines/reference/contextualTypeWithTuple.errors.txt
+++ b/tests/baselines/reference/contextualTypeWithTuple.errors.txt
@@ -18,7 +18,6 @@ tests/cases/conformance/types/tuple/contextualTypeWithTuple.ts(24,1): error TS23
   Property '2' is missing in type '[C, string | number]'.
 tests/cases/conformance/types/tuple/contextualTypeWithTuple.ts(25,1): error TS2322: Type '[number, string | number]' is not assignable to type '[number, string]'.
   Type 'string | number' is not assignable to type 'string'.
-    Type 'number' is not assignable to type 'string'.
 
 
 ==== tests/cases/conformance/types/tuple/contextualTypeWithTuple.ts (7 errors) ====
@@ -73,5 +72,4 @@ tests/cases/conformance/types/tuple/contextualTypeWithTuple.ts(25,1): error TS23
     numStrTuple = unionTuple3;
     ~~~~~~~~~~~
 !!! error TS2322: Type '[number, string | number]' is not assignable to type '[number, string]'.
-!!! error TS2322:   Type 'string | number' is not assignable to type 'string'.
-!!! error TS2322:     Type 'number' is not assignable to type 'string'.
\ No newline at end of file
+!!! error TS2322:   Type 'string | number' is not assignable to type 'string'.
\ No newline at end of file
diff --git a/tests/baselines/reference/contextualTypeWithUnionTypeObjectLiteral.errors.txt b/tests/baselines/reference/contextualTypeWithUnionTypeObjectLiteral.errors.txt
index 651d4f5381f4d..cab098a34398e 100644
--- a/tests/baselines/reference/contextualTypeWithUnionTypeObjectLiteral.errors.txt
+++ b/tests/baselines/reference/contextualTypeWithUnionTypeObjectLiteral.errors.txt
@@ -7,12 +7,10 @@ tests/cases/conformance/types/union/contextualTypeWithUnionTypeObjectLiteral.ts(
   Type '{ prop: string | number; }' is not assignable to type '{ prop: number; }'.
     Types of property 'prop' are incompatible.
       Type 'string | number' is not assignable to type 'number'.
-        Type 'string' is not assignable to type 'number'.
 tests/cases/conformance/types/union/contextualTypeWithUnionTypeObjectLiteral.ts(21,5): error TS2322: Type '{ prop: string | number; anotherP: string; }' is not assignable to type '{ prop: string; anotherP: string; } | { prop: number; }'.
   Type '{ prop: string | number; anotherP: string; }' is not assignable to type '{ prop: number; }'.
     Types of property 'prop' are incompatible.
       Type 'string | number' is not assignable to type 'number'.
-        Type 'string' is not assignable to type 'number'.
 tests/cases/conformance/types/union/contextualTypeWithUnionTypeObjectLiteral.ts(25,5): error TS2322: Type '{ prop: string | number; anotherP: string; }' is not assignable to type '{ prop: string; anotherP: string; } | { prop: number; anotherP1: number; }'.
   Type '{ prop: string | number; anotherP: string; }' is not assignable to type '{ prop: number; anotherP1: number; }'.
     Property 'anotherP1' is missing in type '{ prop: string | number; anotherP: string; }'.
@@ -20,13 +18,11 @@ tests/cases/conformance/types/union/contextualTypeWithUnionTypeObjectLiteral.ts(
   Type '{ prop: string | number; anotherP: string; anotherP1: number; }' is not assignable to type '{ prop: number; anotherP1: number; }'.
     Types of property 'prop' are incompatible.
       Type 'string | number' is not assignable to type 'number'.
-        Type 'string' is not assignable to type 'number'.
 tests/cases/conformance/types/union/contextualTypeWithUnionTypeObjectLiteral.ts(57,5): error TS2322: Type '{ commonMethodDifferentReturnType: (a: string, b: number) => string | number; }' is not assignable to type 'I11 | I21'.
   Type '{ commonMethodDifferentReturnType: (a: string, b: number) => string | number; }' is not assignable to type 'I21'.
     Types of property 'commonMethodDifferentReturnType' are incompatible.
       Type '(a: string, b: number) => string | number' is not assignable to type '(a: string, b: number) => number'.
         Type 'string | number' is not assignable to type 'number'.
-          Type 'string' is not assignable to type 'number'.
 
 
 ==== tests/cases/conformance/types/union/contextualTypeWithUnionTypeObjectLiteral.ts (6 errors) ====
@@ -61,14 +57,12 @@ tests/cases/conformance/types/union/contextualTypeWithUnionTypeObjectLiteral.ts(
 !!! error TS2322:   Type '{ prop: string | number; }' is not assignable to type '{ prop: number; }'.
 !!! error TS2322:     Types of property 'prop' are incompatible.
 !!! error TS2322:       Type 'string | number' is not assignable to type 'number'.
-!!! error TS2322:         Type 'string' is not assignable to type 'number'.
     var objStrOrNum6: { prop: string; anotherP: string; } | { prop: number } = {
         ~~~~~~~~~~~~
 !!! error TS2322: Type '{ prop: string | number; anotherP: string; }' is not assignable to type '{ prop: string; anotherP: string; } | { prop: number; }'.
 !!! error TS2322:   Type '{ prop: string | number; anotherP: string; }' is not assignable to type '{ prop: number; }'.
 !!! error TS2322:     Types of property 'prop' are incompatible.
 !!! error TS2322:       Type 'string | number' is not assignable to type 'number'.
-!!! error TS2322:         Type 'string' is not assignable to type 'number'.
         prop: strOrNumber,
         anotherP: str
     };
@@ -86,7 +80,6 @@ tests/cases/conformance/types/union/contextualTypeWithUnionTypeObjectLiteral.ts(
 !!! error TS2322:   Type '{ prop: string | number; anotherP: string; anotherP1: number; }' is not assignable to type '{ prop: number; anotherP1: number; }'.
 !!! error TS2322:     Types of property 'prop' are incompatible.
 !!! error TS2322:       Type 'string | number' is not assignable to type 'number'.
-!!! error TS2322:         Type 'string' is not assignable to type 'number'.
         prop: strOrNumber,
         anotherP: str,
         anotherP1: num
@@ -121,6 +114,5 @@ tests/cases/conformance/types/union/contextualTypeWithUnionTypeObjectLiteral.ts(
 !!! error TS2322:     Types of property 'commonMethodDifferentReturnType' are incompatible.
 !!! error TS2322:       Type '(a: string, b: number) => string | number' is not assignable to type '(a: string, b: number) => number'.
 !!! error TS2322:         Type 'string | number' is not assignable to type 'number'.
-!!! error TS2322:           Type 'string' is not assignable to type 'number'.
         commonMethodDifferentReturnType: (a, b) => strOrNumber,
     };
\ No newline at end of file
diff --git a/tests/baselines/reference/controlFlowIterationErrors.errors.txt b/tests/baselines/reference/controlFlowIterationErrors.errors.txt
index 28cbf8bdc478a..857ad73eb7793 100644
--- a/tests/baselines/reference/controlFlowIterationErrors.errors.txt
+++ b/tests/baselines/reference/controlFlowIterationErrors.errors.txt
@@ -1,11 +1,9 @@
 tests/cases/conformance/controlFlow/controlFlowIterationErrors.ts(11,17): error TS2345: Argument of type 'string | number' is not assignable to parameter of type 'string'.
   Type 'number' is not assignable to type 'string'.
 tests/cases/conformance/controlFlow/controlFlowIterationErrors.ts(22,17): error TS2345: Argument of type 'string | number' is not assignable to parameter of type 'string'.
-  Type 'number' is not assignable to type 'string'.
 tests/cases/conformance/controlFlow/controlFlowIterationErrors.ts(34,17): error TS2345: Argument of type 'string | number' is not assignable to parameter of type 'number'.
   Type 'string' is not assignable to type 'number'.
 tests/cases/conformance/controlFlow/controlFlowIterationErrors.ts(45,17): error TS2345: Argument of type 'string | number' is not assignable to parameter of type 'number'.
-  Type 'string' is not assignable to type 'number'.
 
 
 ==== tests/cases/conformance/controlFlow/controlFlowIterationErrors.ts (4 errors) ====
@@ -36,7 +34,6 @@ tests/cases/conformance/controlFlow/controlFlowIterationErrors.ts(45,17): error
             x = len(x);
                     ~
 !!! error TS2345: Argument of type 'string | number' is not assignable to parameter of type 'string'.
-!!! error TS2345:   Type 'number' is not assignable to type 'string'.
         }
         x;
     }
@@ -65,7 +62,6 @@ tests/cases/conformance/controlFlow/controlFlowIterationErrors.ts(45,17): error
             x = foo(x);
                     ~
 !!! error TS2345: Argument of type 'string | number' is not assignable to parameter of type 'number'.
-!!! error TS2345:   Type 'string' is not assignable to type 'number'.
         }
         x;
     }
diff --git a/tests/baselines/reference/keyofAndIndexedAccessErrors.errors.txt b/tests/baselines/reference/keyofAndIndexedAccessErrors.errors.txt
index 0634c3419e014..88d9c2295806c 100644
--- a/tests/baselines/reference/keyofAndIndexedAccessErrors.errors.txt
+++ b/tests/baselines/reference/keyofAndIndexedAccessErrors.errors.txt
@@ -21,7 +21,6 @@ tests/cases/conformance/types/keyof/keyofAndIndexedAccessErrors.ts(64,33): error
   Type '"size"' is not assignable to type '"name" | "width" | "height" | "visible"'.
 tests/cases/conformance/types/keyof/keyofAndIndexedAccessErrors.ts(66,24): error TS2345: Argument of type '"size"' is not assignable to parameter of type '"name" | "width" | "height" | "visible"'.
 tests/cases/conformance/types/keyof/keyofAndIndexedAccessErrors.ts(67,24): error TS2345: Argument of type '"name" | "size"' is not assignable to parameter of type '"name" | "width" | "height" | "visible"'.
-  Type '"size"' is not assignable to type '"name" | "width" | "height" | "visible"'.
 tests/cases/conformance/types/keyof/keyofAndIndexedAccessErrors.ts(72,5): error TS2536: Type 'keyof (T & U)' cannot be used to index type 'T | U'.
 tests/cases/conformance/types/keyof/keyofAndIndexedAccessErrors.ts(76,5): error TS2322: Type 'T | U' is not assignable to type 'T & U'.
   Type 'T' is not assignable to type 'T & U'.
@@ -142,7 +141,6 @@ tests/cases/conformance/types/keyof/keyofAndIndexedAccessErrors.ts(77,5): error
         setProperty(shape, cond ? "name" : "size", 10);  // Error
                            ~~~~~~~~~~~~~~~~~~~~~~
 !!! error TS2345: Argument of type '"name" | "size"' is not assignable to parameter of type '"name" | "width" | "height" | "visible"'.
-!!! error TS2345:   Type '"size"' is not assignable to type '"name" | "width" | "height" | "visible"'.
     }
     
     function f20<T, U>(k1: keyof (T | U), k2: keyof (T & U), o1: T | U, o2: T & U) {
diff --git a/tests/baselines/reference/mappedTypeRelationships.errors.txt b/tests/baselines/reference/mappedTypeRelationships.errors.txt
index 1ea0c5a26123a..54e2253442334 100644
--- a/tests/baselines/reference/mappedTypeRelationships.errors.txt
+++ b/tests/baselines/reference/mappedTypeRelationships.errors.txt
@@ -50,16 +50,15 @@ tests/cases/conformance/types/mapped/mappedTypeRelationships.ts(40,5): error TS2
 tests/cases/conformance/types/mapped/mappedTypeRelationships.ts(41,5): error TS2322: Type 'T[keyof T]' is not assignable to type 'Partial<U>[keyof T]'.
   Type 'T[string]' is not assignable to type 'Partial<U>[keyof T]'.
     Type 'T[string]' is not assignable to type 'U[keyof T] | undefined'.
-      Type 'T[string]' is not assignable to type 'U[keyof T]'.
-        Type 'T[keyof T]' is not assignable to type 'U[keyof T] | undefined'.
-          Type 'T[string]' is not assignable to type 'U[keyof T] | undefined'.
-            Type 'T[string]' is not assignable to type 'U[keyof T]'.
-              Type 'T[keyof T]' is not assignable to type 'U[keyof T]'.
-                Type 'T[string]' is not assignable to type 'U[keyof T]'.
-                  Type 'T[string]' is not assignable to type 'U[string]'.
-                    Type 'T[keyof T]' is not assignable to type 'U[string]'.
-                      Type 'T[string]' is not assignable to type 'U[string]'.
-                        Type 'T' is not assignable to type 'U'.
+      Type 'T[keyof T]' is not assignable to type 'U[keyof T] | undefined'.
+        Type 'T[string]' is not assignable to type 'U[keyof T] | undefined'.
+          Type 'T[string]' is not assignable to type 'U[keyof T]'.
+            Type 'T[keyof T]' is not assignable to type 'U[keyof T]'.
+              Type 'T[string]' is not assignable to type 'U[keyof T]'.
+                Type 'T[string]' is not assignable to type 'U[string]'.
+                  Type 'T[keyof T]' is not assignable to type 'U[string]'.
+                    Type 'T[string]' is not assignable to type 'U[string]'.
+                      Type 'T' is not assignable to type 'U'.
 tests/cases/conformance/types/mapped/mappedTypeRelationships.ts(45,5): error TS2322: Type 'Partial<U>[K]' is not assignable to type 'T[K]'.
   Type 'U[K] | undefined' is not assignable to type 'T[K]'.
     Type 'undefined' is not assignable to type 'T[K]'.
@@ -70,16 +69,15 @@ tests/cases/conformance/types/mapped/mappedTypeRelationships.ts(45,5): error TS2
 tests/cases/conformance/types/mapped/mappedTypeRelationships.ts(46,5): error TS2322: Type 'T[K]' is not assignable to type 'Partial<U>[K]'.
   Type 'T[string]' is not assignable to type 'Partial<U>[K]'.
     Type 'T[string]' is not assignable to type 'U[K] | undefined'.
-      Type 'T[string]' is not assignable to type 'U[K]'.
-        Type 'T[K]' is not assignable to type 'U[K] | undefined'.
-          Type 'T[string]' is not assignable to type 'U[K] | undefined'.
-            Type 'T[string]' is not assignable to type 'U[K]'.
-              Type 'T[K]' is not assignable to type 'U[K]'.
-                Type 'T[string]' is not assignable to type 'U[K]'.
-                  Type 'T[string]' is not assignable to type 'U[string]'.
-                    Type 'T[K]' is not assignable to type 'U[string]'.
-                      Type 'T[string]' is not assignable to type 'U[string]'.
-                        Type 'T' is not assignable to type 'U'.
+      Type 'T[K]' is not assignable to type 'U[K] | undefined'.
+        Type 'T[string]' is not assignable to type 'U[K] | undefined'.
+          Type 'T[string]' is not assignable to type 'U[K]'.
+            Type 'T[K]' is not assignable to type 'U[K]'.
+              Type 'T[string]' is not assignable to type 'U[K]'.
+                Type 'T[string]' is not assignable to type 'U[string]'.
+                  Type 'T[K]' is not assignable to type 'U[string]'.
+                    Type 'T[string]' is not assignable to type 'U[string]'.
+                      Type 'T' is not assignable to type 'U'.
 tests/cases/conformance/types/mapped/mappedTypeRelationships.ts(51,5): error TS2542: Index signature in type 'Readonly<T>' only permits reading.
 tests/cases/conformance/types/mapped/mappedTypeRelationships.ts(56,5): error TS2542: Index signature in type 'Readonly<T>' only permits reading.
 tests/cases/conformance/types/mapped/mappedTypeRelationships.ts(61,5): error TS2322: Type 'T[keyof T]' is not assignable to type 'Readonly<U>[keyof T]'.
@@ -236,16 +234,15 @@ tests/cases/conformance/types/mapped/mappedTypeRelationships.ts(168,5): error TS
 !!! error TS2322: Type 'T[keyof T]' is not assignable to type 'Partial<U>[keyof T]'.
 !!! error TS2322:   Type 'T[string]' is not assignable to type 'Partial<U>[keyof T]'.
 !!! error TS2322:     Type 'T[string]' is not assignable to type 'U[keyof T] | undefined'.
-!!! error TS2322:       Type 'T[string]' is not assignable to type 'U[keyof T]'.
-!!! error TS2322:         Type 'T[keyof T]' is not assignable to type 'U[keyof T] | undefined'.
-!!! error TS2322:           Type 'T[string]' is not assignable to type 'U[keyof T] | undefined'.
-!!! error TS2322:             Type 'T[string]' is not assignable to type 'U[keyof T]'.
-!!! error TS2322:               Type 'T[keyof T]' is not assignable to type 'U[keyof T]'.
-!!! error TS2322:                 Type 'T[string]' is not assignable to type 'U[keyof T]'.
-!!! error TS2322:                   Type 'T[string]' is not assignable to type 'U[string]'.
-!!! error TS2322:                     Type 'T[keyof T]' is not assignable to type 'U[string]'.
-!!! error TS2322:                       Type 'T[string]' is not assignable to type 'U[string]'.
-!!! error TS2322:                         Type 'T' is not assignable to type 'U'.
+!!! error TS2322:       Type 'T[keyof T]' is not assignable to type 'U[keyof T] | undefined'.
+!!! error TS2322:         Type 'T[string]' is not assignable to type 'U[keyof T] | undefined'.
+!!! error TS2322:           Type 'T[string]' is not assignable to type 'U[keyof T]'.
+!!! error TS2322:             Type 'T[keyof T]' is not assignable to type 'U[keyof T]'.
+!!! error TS2322:               Type 'T[string]' is not assignable to type 'U[keyof T]'.
+!!! error TS2322:                 Type 'T[string]' is not assignable to type 'U[string]'.
+!!! error TS2322:                   Type 'T[keyof T]' is not assignable to type 'U[string]'.
+!!! error TS2322:                     Type 'T[string]' is not assignable to type 'U[string]'.
+!!! error TS2322:                       Type 'T' is not assignable to type 'U'.
     }
     
     function f13<T, U extends T, K extends keyof T>(x: T, y: Partial<U>, k: K) {
@@ -263,16 +260,15 @@ tests/cases/conformance/types/mapped/mappedTypeRelationships.ts(168,5): error TS
 !!! error TS2322: Type 'T[K]' is not assignable to type 'Partial<U>[K]'.
 !!! error TS2322:   Type 'T[string]' is not assignable to type 'Partial<U>[K]'.
 !!! error TS2322:     Type 'T[string]' is not assignable to type 'U[K] | undefined'.
-!!! error TS2322:       Type 'T[string]' is not assignable to type 'U[K]'.
-!!! error TS2322:         Type 'T[K]' is not assignable to type 'U[K] | undefined'.
-!!! error TS2322:           Type 'T[string]' is not assignable to type 'U[K] | undefined'.
-!!! error TS2322:             Type 'T[string]' is not assignable to type 'U[K]'.
-!!! error TS2322:               Type 'T[K]' is not assignable to type 'U[K]'.
-!!! error TS2322:                 Type 'T[string]' is not assignable to type 'U[K]'.
-!!! error TS2322:                   Type 'T[string]' is not assignable to type 'U[string]'.
-!!! error TS2322:                     Type 'T[K]' is not assignable to type 'U[string]'.
-!!! error TS2322:                       Type 'T[string]' is not assignable to type 'U[string]'.
-!!! error TS2322:                         Type 'T' is not assignable to type 'U'.
+!!! error TS2322:       Type 'T[K]' is not assignable to type 'U[K] | undefined'.
+!!! error TS2322:         Type 'T[string]' is not assignable to type 'U[K] | undefined'.
+!!! error TS2322:           Type 'T[string]' is not assignable to type 'U[K]'.
+!!! error TS2322:             Type 'T[K]' is not assignable to type 'U[K]'.
+!!! error TS2322:               Type 'T[string]' is not assignable to type 'U[K]'.
+!!! error TS2322:                 Type 'T[string]' is not assignable to type 'U[string]'.
+!!! error TS2322:                   Type 'T[K]' is not assignable to type 'U[string]'.
+!!! error TS2322:                     Type 'T[string]' is not assignable to type 'U[string]'.
+!!! error TS2322:                       Type 'T' is not assignable to type 'U'.
     }
     
     function f20<T>(x: T, y: Readonly<T>, k: keyof T) {
diff --git a/tests/baselines/reference/nonPrimitiveStrictNull.errors.txt b/tests/baselines/reference/nonPrimitiveStrictNull.errors.txt
index 6b26c4d42ac8c..d162592d36e3f 100644
--- a/tests/baselines/reference/nonPrimitiveStrictNull.errors.txt
+++ b/tests/baselines/reference/nonPrimitiveStrictNull.errors.txt
@@ -9,7 +9,6 @@ tests/cases/conformance/types/nonPrimitive/nonPrimitiveStrictNull.ts(11,1): erro
   Type 'undefined' is not assignable to type 'object'.
 tests/cases/conformance/types/nonPrimitive/nonPrimitiveStrictNull.ts(17,7): error TS2339: Property 'toString' does not exist on type 'never'.
 tests/cases/conformance/types/nonPrimitive/nonPrimitiveStrictNull.ts(21,5): error TS2322: Type 'object | null' is not assignable to type 'object'.
-  Type 'null' is not assignable to type 'object'.
 tests/cases/conformance/types/nonPrimitive/nonPrimitiveStrictNull.ts(26,5): error TS2531: Object is possibly 'null'.
 tests/cases/conformance/types/nonPrimitive/nonPrimitiveStrictNull.ts(28,5): error TS2532: Object is possibly 'undefined'.
 tests/cases/conformance/types/nonPrimitive/nonPrimitiveStrictNull.ts(32,5): error TS2533: Object is possibly 'null' or 'undefined'.
@@ -63,7 +62,6 @@ tests/cases/conformance/types/nonPrimitive/nonPrimitiveStrictNull.ts(53,14): err
         a = b; // error, b is not narrowed
         ~
 !!! error TS2322: Type 'object | null' is not assignable to type 'object'.
-!!! error TS2322:   Type 'null' is not assignable to type 'object'.
     }
     
     if (typeof d === 'object') {
diff --git a/tests/baselines/reference/objectSpreadStrictNull.errors.txt b/tests/baselines/reference/objectSpreadStrictNull.errors.txt
index 791b5419eb1bc..00fd80895f189 100644
--- a/tests/baselines/reference/objectSpreadStrictNull.errors.txt
+++ b/tests/baselines/reference/objectSpreadStrictNull.errors.txt
@@ -5,7 +5,6 @@ tests/cases/conformance/types/spread/objectSpreadStrictNull.ts(14,9): error TS23
 tests/cases/conformance/types/spread/objectSpreadStrictNull.ts(15,9): error TS2322: Type '{ sn: number | undefined; }' is not assignable to type '{ sn: string | number; }'.
   Types of property 'sn' are incompatible.
     Type 'number | undefined' is not assignable to type 'string | number'.
-      Type 'undefined' is not assignable to type 'string | number'.
 tests/cases/conformance/types/spread/objectSpreadStrictNull.ts(18,9): error TS2322: Type '{ sn: string | number | undefined; }' is not assignable to type '{ sn: string | number | boolean; }'.
   Types of property 'sn' are incompatible.
     Type 'string | number | undefined' is not assignable to type 'string | number | boolean'.
@@ -44,7 +43,6 @@ tests/cases/conformance/types/spread/objectSpreadStrictNull.ts(42,5): error TS23
 !!! error TS2322: Type '{ sn: number | undefined; }' is not assignable to type '{ sn: string | number; }'.
 !!! error TS2322:   Types of property 'sn' are incompatible.
 !!! error TS2322:     Type 'number | undefined' is not assignable to type 'string | number'.
-!!! error TS2322:       Type 'undefined' is not assignable to type 'string | number'.
         let allUndefined: { sn: string | number | undefined } = { ...undefinedString, ...undefinedNumber };
     
         let undefinedWithOptionalContinues: { sn: string | number | boolean } = { ...definiteBoolean, ...undefinedString, ...optionalNumber };
diff --git a/tests/baselines/reference/stringLiteralsWithSwitchStatements03.errors.txt b/tests/baselines/reference/stringLiteralsWithSwitchStatements03.errors.txt
index a16be70295597..6447f1106e435 100644
--- a/tests/baselines/reference/stringLiteralsWithSwitchStatements03.errors.txt
+++ b/tests/baselines/reference/stringLiteralsWithSwitchStatements03.errors.txt
@@ -5,11 +5,9 @@ tests/cases/conformance/types/literal/stringLiteralsWithSwitchStatements03.ts(14
 tests/cases/conformance/types/literal/stringLiteralsWithSwitchStatements03.ts(14,11): error TS2695: Left side of comma operator is unused and has no side effects.
 tests/cases/conformance/types/literal/stringLiteralsWithSwitchStatements03.ts(14,11): error TS2695: Left side of comma operator is unused and has no side effects.
 tests/cases/conformance/types/literal/stringLiteralsWithSwitchStatements03.ts(20,10): error TS2678: Type '"bar" | "baz"' is not comparable to type '"foo"'.
-  Type '"baz"' is not comparable to type '"foo"'.
 tests/cases/conformance/types/literal/stringLiteralsWithSwitchStatements03.ts(22,10): error TS2678: Type '"bar" | "baz"' is not comparable to type '"foo"'.
   Type '"baz"' is not comparable to type '"foo"'.
 tests/cases/conformance/types/literal/stringLiteralsWithSwitchStatements03.ts(23,10): error TS2678: Type '"bar" | "baz"' is not comparable to type '"foo"'.
-  Type '"baz"' is not comparable to type '"foo"'.
 
 
 ==== tests/cases/conformance/types/literal/stringLiteralsWithSwitchStatements03.ts (8 errors) ====
@@ -46,7 +44,6 @@ tests/cases/conformance/types/literal/stringLiteralsWithSwitchStatements03.ts(23
         case (("bar" || ("baz"))):
              ~~~~~~~~~~~~~~~~~~~~
 !!! error TS2678: Type '"bar" | "baz"' is not comparable to type '"foo"'.
-!!! error TS2678:   Type '"baz"' is not comparable to type '"foo"'.
             break;
         case z || "baz":
              ~~~~~~~~~~
@@ -55,7 +52,6 @@ tests/cases/conformance/types/literal/stringLiteralsWithSwitchStatements03.ts(23
         case "baz" || z:
              ~~~~~~~~~~
 !!! error TS2678: Type '"bar" | "baz"' is not comparable to type '"foo"'.
-!!! error TS2678:   Type '"baz"' is not comparable to type '"foo"'.
             z;
             break;
     }
diff --git a/tests/baselines/reference/typeArgumentsWithStringLiteralTypes01.errors.txt b/tests/baselines/reference/typeArgumentsWithStringLiteralTypes01.errors.txt
index fa9231635e435..43242c537967a 100644
--- a/tests/baselines/reference/typeArgumentsWithStringLiteralTypes01.errors.txt
+++ b/tests/baselines/reference/typeArgumentsWithStringLiteralTypes01.errors.txt
@@ -16,16 +16,13 @@ tests/cases/conformance/types/stringLiteral/typeArgumentsWithStringLiteralTypes0
 tests/cases/conformance/types/stringLiteral/typeArgumentsWithStringLiteralTypes01.ts(74,5): error TS2322: Type '"Hello" | "World"' is not assignable to type '"Hello"'.
   Type '"World"' is not assignable to type '"Hello"'.
 tests/cases/conformance/types/stringLiteral/typeArgumentsWithStringLiteralTypes01.ts(76,5): error TS2322: Type '"Hello" | "World"' is not assignable to type '"Hello"'.
-  Type '"World"' is not assignable to type '"Hello"'.
 tests/cases/conformance/types/stringLiteral/typeArgumentsWithStringLiteralTypes01.ts(86,43): error TS2345: Argument of type '"World"' is not assignable to parameter of type '"Hello"'.
 tests/cases/conformance/types/stringLiteral/typeArgumentsWithStringLiteralTypes01.ts(87,43): error TS2345: Argument of type '"Hello"' is not assignable to parameter of type '"World"'.
 tests/cases/conformance/types/stringLiteral/typeArgumentsWithStringLiteralTypes01.ts(88,52): error TS2345: Argument of type '"World"' is not assignable to parameter of type '"Hello"'.
 tests/cases/conformance/types/stringLiteral/typeArgumentsWithStringLiteralTypes01.ts(92,5): error TS2322: Type 'string' is not assignable to type '"Hello" | "World"'.
 tests/cases/conformance/types/stringLiteral/typeArgumentsWithStringLiteralTypes01.ts(96,5): error TS2322: Type 'string' is not assignable to type '"Hello" | "World"'.
 tests/cases/conformance/types/stringLiteral/typeArgumentsWithStringLiteralTypes01.ts(99,25): error TS2345: Argument of type '"Hello" | "World"' is not assignable to parameter of type '"Hello"'.
-  Type '"World"' is not assignable to type '"Hello"'.
 tests/cases/conformance/types/stringLiteral/typeArgumentsWithStringLiteralTypes01.ts(103,25): error TS2345: Argument of type '"Hello" | "World"' is not assignable to parameter of type '"Hello"'.
-  Type '"World"' is not assignable to type '"Hello"'.
 
 
 ==== tests/cases/conformance/types/stringLiteral/typeArgumentsWithStringLiteralTypes01.ts (24 errors) ====
@@ -140,7 +137,6 @@ tests/cases/conformance/types/stringLiteral/typeArgumentsWithStringLiteralTypes0
         c = takeReturnHelloWorld(c);
         ~
 !!! error TS2322: Type '"Hello" | "World"' is not assignable to type '"Hello"'.
-!!! error TS2322:   Type '"World"' is not assignable to type '"Hello"'.
         d = takeReturnHelloWorld(d);
         e = takeReturnHelloWorld(e);
     }
@@ -176,14 +172,12 @@ tests/cases/conformance/types/stringLiteral/typeArgumentsWithStringLiteralTypes0
         a = takeReturnHello(a);
                             ~
 !!! error TS2345: Argument of type '"Hello" | "World"' is not assignable to parameter of type '"Hello"'.
-!!! error TS2345:   Type '"World"' is not assignable to type '"Hello"'.
         b = takeReturnHello(b);
         c = takeReturnHello(c);
         d = takeReturnHello(d);
         e = takeReturnHello(e);
                             ~
 !!! error TS2345: Argument of type '"Hello" | "World"' is not assignable to parameter of type '"Hello"'.
-!!! error TS2345:   Type '"World"' is not assignable to type '"Hello"'.
     
         // Both should be valid.
         a = takeReturnHelloWorld(a);
diff --git a/tests/baselines/reference/typeParameterDiamond2.errors.txt b/tests/baselines/reference/typeParameterDiamond2.errors.txt
index f268724c6efaa..42224fe35771a 100644
--- a/tests/baselines/reference/typeParameterDiamond2.errors.txt
+++ b/tests/baselines/reference/typeParameterDiamond2.errors.txt
@@ -2,7 +2,6 @@ tests/cases/compiler/typeParameterDiamond2.ts(8,13): error TS2322: Type 'T | U'
   Type 'U' is not assignable to type 'Top'.
 tests/cases/compiler/typeParameterDiamond2.ts(10,13): error TS2322: Type 'Bottom' is not assignable to type 'Top'.
   Type 'T | U' is not assignable to type 'Top'.
-    Type 'U' is not assignable to type 'Top'.
 
 
 ==== tests/cases/compiler/typeParameterDiamond2.ts (2 errors) ====
@@ -22,7 +21,6 @@ tests/cases/compiler/typeParameterDiamond2.ts(10,13): error TS2322: Type 'Bottom
                 ~~~
 !!! error TS2322: Type 'Bottom' is not assignable to type 'Top'.
 !!! error TS2322:   Type 'T | U' is not assignable to type 'Top'.
-!!! error TS2322:     Type 'U' is not assignable to type 'Top'.
             }
         }
     }
\ No newline at end of file
diff --git a/tests/baselines/reference/typeParameterDiamond4.errors.txt b/tests/baselines/reference/typeParameterDiamond4.errors.txt
index 2a7fbdaf15c9f..ff75093ab2df2 100644
--- a/tests/baselines/reference/typeParameterDiamond4.errors.txt
+++ b/tests/baselines/reference/typeParameterDiamond4.errors.txt
@@ -2,7 +2,6 @@ tests/cases/compiler/typeParameterDiamond4.ts(8,13): error TS2322: Type 'Top | T
   Type 'T' is not assignable to type 'Top'.
 tests/cases/compiler/typeParameterDiamond4.ts(10,13): error TS2322: Type 'Bottom' is not assignable to type 'Top'.
   Type 'Top | T | U' is not assignable to type 'Top'.
-    Type 'T' is not assignable to type 'Top'.
 
 
 ==== tests/cases/compiler/typeParameterDiamond4.ts (2 errors) ====
@@ -22,7 +21,6 @@ tests/cases/compiler/typeParameterDiamond4.ts(10,13): error TS2322: Type 'Bottom
                 ~~~
 !!! error TS2322: Type 'Bottom' is not assignable to type 'Top'.
 !!! error TS2322:   Type 'Top | T | U' is not assignable to type 'Top'.
-!!! error TS2322:     Type 'T' is not assignable to type 'Top'.
             }
         }
     }
\ No newline at end of file