diff --git a/src/compiler/checker.ts b/src/compiler/checker.ts
index ac02f917827e4..ba7bf191be784 100644
--- a/src/compiler/checker.ts
+++ b/src/compiler/checker.ts
@@ -16540,7 +16540,7 @@ namespace ts {
                             if (!targetProperty) continue outer;
                             if (sourceProperty === targetProperty) continue;
                             // We compare the source property to the target in the context of a single discriminant type.
-                            const related = propertyRelatedTo(source, target, sourceProperty, targetProperty, _ => combination[i], /*reportErrors*/ false, IntersectionState.None);
+                            const related = propertyRelatedTo(source, target, sourceProperty, targetProperty, _ => combination[i], /*reportErrors*/ false, IntersectionState.None, /*skipOptional*/ strictNullChecks || relation === comparableRelation);
                             // If the target property could not be found, or if the properties were not related,
                             // then this constituent is not a match.
                             if (!related) {
@@ -16638,7 +16638,7 @@ namespace ts {
                 }
             }
 
-            function propertyRelatedTo(source: Type, target: Type, sourceProp: Symbol, targetProp: Symbol, getTypeOfSourceProperty: (sym: Symbol) => Type, reportErrors: boolean, intersectionState: IntersectionState): Ternary {
+            function propertyRelatedTo(source: Type, target: Type, sourceProp: Symbol, targetProp: Symbol, getTypeOfSourceProperty: (sym: Symbol) => Type, reportErrors: boolean, intersectionState: IntersectionState, skipOptional: boolean): Ternary {
                 const sourcePropFlags = getDeclarationModifierFlagsFromSymbol(sourceProp);
                 const targetPropFlags = getDeclarationModifierFlagsFromSymbol(targetProp);
                 if (sourcePropFlags & ModifierFlags.Private || targetPropFlags & ModifierFlags.Private) {
@@ -16681,7 +16681,7 @@ namespace ts {
                     return Ternary.False;
                 }
                 // When checking for comparability, be more lenient with optional properties.
-                if (relation !== comparableRelation && sourceProp.flags & SymbolFlags.Optional && !(targetProp.flags & SymbolFlags.Optional)) {
+                if (!skipOptional && sourceProp.flags & SymbolFlags.Optional && !(targetProp.flags & SymbolFlags.Optional)) {
                     // TypeScript 1.0 spec (April 2014): 3.8.3
                     // S is a subtype of a type T, and T is a supertype of S if ...
                     // S' and T are object types and, for each member M in T..
@@ -16811,7 +16811,7 @@ namespace ts {
                     if (!(targetProp.flags & SymbolFlags.Prototype) && (!numericNamesOnly || isNumericLiteralName(name) || name === "length")) {
                         const sourceProp = getPropertyOfType(source, name);
                         if (sourceProp && sourceProp !== targetProp) {
-                            const related = propertyRelatedTo(source, target, sourceProp, targetProp, getTypeOfSymbol, reportErrors, intersectionState);
+                            const related = propertyRelatedTo(source, target, sourceProp, targetProp, getTypeOfSymbol, reportErrors, intersectionState, relation === comparableRelation);
                             if (!related) {
                                 return Ternary.False;
                             }
diff --git a/tests/baselines/reference/unionRelationshipCheckPasses.js b/tests/baselines/reference/unionRelationshipCheckPasses.js
new file mode 100644
index 0000000000000..65e90ed34e811
--- /dev/null
+++ b/tests/baselines/reference/unionRelationshipCheckPasses.js
@@ -0,0 +1,7 @@
+//// [unionRelationshipCheckPasses.ts]
+const item: { foo?: undefined } | { foo: number } = null as any as { foo?: number | undefined };
+
+
+//// [unionRelationshipCheckPasses.js]
+"use strict";
+var item = null;
diff --git a/tests/baselines/reference/unionRelationshipCheckPasses.symbols b/tests/baselines/reference/unionRelationshipCheckPasses.symbols
new file mode 100644
index 0000000000000..3fda4578bdbb3
--- /dev/null
+++ b/tests/baselines/reference/unionRelationshipCheckPasses.symbols
@@ -0,0 +1,7 @@
+=== tests/cases/compiler/unionRelationshipCheckPasses.ts ===
+const item: { foo?: undefined } | { foo: number } = null as any as { foo?: number | undefined };
+>item : Symbol(item, Decl(unionRelationshipCheckPasses.ts, 0, 5))
+>foo : Symbol(foo, Decl(unionRelationshipCheckPasses.ts, 0, 13))
+>foo : Symbol(foo, Decl(unionRelationshipCheckPasses.ts, 0, 35))
+>foo : Symbol(foo, Decl(unionRelationshipCheckPasses.ts, 0, 68))
+
diff --git a/tests/baselines/reference/unionRelationshipCheckPasses.types b/tests/baselines/reference/unionRelationshipCheckPasses.types
new file mode 100644
index 0000000000000..e0e582916bb9c
--- /dev/null
+++ b/tests/baselines/reference/unionRelationshipCheckPasses.types
@@ -0,0 +1,10 @@
+=== tests/cases/compiler/unionRelationshipCheckPasses.ts ===
+const item: { foo?: undefined } | { foo: number } = null as any as { foo?: number | undefined };
+>item : { foo?: undefined; } | { foo: number; }
+>foo : undefined
+>foo : number
+>null as any as { foo?: number | undefined } : { foo?: number | undefined; }
+>null as any : any
+>null : null
+>foo : number | undefined
+
diff --git a/tests/cases/compiler/unionRelationshipCheckPasses.ts b/tests/cases/compiler/unionRelationshipCheckPasses.ts
new file mode 100644
index 0000000000000..cec4cffbf08cd
--- /dev/null
+++ b/tests/cases/compiler/unionRelationshipCheckPasses.ts
@@ -0,0 +1,2 @@
+// @strict: true
+const item: { foo?: undefined } | { foo: number } = null as any as { foo?: number | undefined };