diff --git a/src/compiler/checker.ts b/src/compiler/checker.ts
index c1eb3ea2ddcdd..453ea33eeb60f 100644
--- a/src/compiler/checker.ts
+++ b/src/compiler/checker.ts
@@ -756,12 +756,7 @@ namespace ts {
         falseType.freshType = falseType;
         regularFalseType.regularType = regularFalseType;
         regularFalseType.freshType = falseType;
-        const booleanType = createBooleanType([regularFalseType, regularTrueType]);
-        // Also mark all combinations of fresh/regular booleans as "Boolean" so they print as `boolean` instead of `true | false`
-        // (The union is cached, so simply doing the marking here is sufficient)
-        createBooleanType([regularFalseType, trueType]);
-        createBooleanType([falseType, regularTrueType]);
-        createBooleanType([falseType, trueType]);
+        const booleanType = getUnionType([regularFalseType, regularTrueType]);
         const esSymbolType = createIntrinsicType(TypeFlags.ESSymbol, "symbol");
         const voidType = createIntrinsicType(TypeFlags.Void, "void");
         const neverType = createIntrinsicType(TypeFlags.Never, "never");
@@ -3836,13 +3831,6 @@ namespace ts {
             return type;
         }
 
-        function createBooleanType(trueFalseTypes: readonly Type[]): IntrinsicType & UnionType {
-            const type = getUnionType(trueFalseTypes) as IntrinsicType & UnionType;
-            type.flags |= TypeFlags.Boolean;
-            type.intrinsicName = "boolean";
-            return type;
-        }
-
         function createObjectType(objectFlags: ObjectFlags, symbol?: Symbol): ObjectType {
             const type = createType(TypeFlags.Object) as ObjectType;
             type.objectFlags = objectFlags;
@@ -4583,7 +4571,7 @@ namespace ts {
                     context.approximateLength += 6;
                     return factory.createKeywordTypeNode(SyntaxKind.BigIntKeyword);
                 }
-                if (type.flags & TypeFlags.Boolean) {
+                if (type.flags & TypeFlags.Boolean && !type.aliasSymbol) {
                     context.approximateLength += 7;
                     return factory.createKeywordTypeNode(SyntaxKind.BooleanKeyword);
                 }
@@ -13974,16 +13962,6 @@ namespace ts {
             return a.kind === b.kind && a.parameterIndex === b.parameterIndex;
         }
 
-        function createUnionType(types: Type[], aliasSymbol?: Symbol, aliasTypeArguments?: readonly Type[], origin?: Type) {
-            const result = createType(TypeFlags.Union) as UnionType;
-            result.objectFlags = getPropagatingFlagsOfTypes(types, /*excludeKinds*/ TypeFlags.Nullable);
-            result.types = types;
-            result.origin = origin;
-            result.aliasSymbol = aliasSymbol;
-            result.aliasTypeArguments = aliasTypeArguments;
-            return result;
-        }
-
         // This function assumes the constituent type list is sorted and deduplicated.
         function getUnionTypeFromSortedList(types: Type[], objectFlags: ObjectFlags, aliasSymbol?: Symbol, aliasTypeArguments?: readonly Type[], origin?: Type): Type {
             if (types.length === 0) {
@@ -13999,8 +13977,16 @@ namespace ts {
             const id = typeKey + getAliasId(aliasSymbol, aliasTypeArguments);
             let type = unionTypes.get(id);
             if (!type) {
-                type = createUnionType(types, aliasSymbol, aliasTypeArguments, origin);
-                type.objectFlags |= objectFlags;
+                type = createType(TypeFlags.Union) as UnionType;
+                type.objectFlags = objectFlags | getPropagatingFlagsOfTypes(types, /*excludeKinds*/ TypeFlags.Nullable);
+                type.types = types;
+                type.origin = origin;
+                type.aliasSymbol = aliasSymbol;
+                type.aliasTypeArguments = aliasTypeArguments;
+                if (types.length === 2 && types[0].flags & TypeFlags.BooleanLiteral && types[1].flags & TypeFlags.BooleanLiteral) {
+                    type.flags |= TypeFlags.Boolean;
+                    (type as UnionType & IntrinsicType).intrinsicName = "boolean";
+                }
                 unionTypes.set(id, type);
             }
             return type;
@@ -17328,8 +17314,8 @@ namespace ts {
                 }
             }
             else {
-                if (!(source.flags & TypeFlags.UnionOrIntersection) && !(target.flags & TypeFlags.UnionOrIntersection) &&
-                    source.flags !== target.flags && !(source.flags & TypeFlags.Substructure)) return false;
+                if (source.flags !== target.flags) return false;
+                if (source.flags & TypeFlags.Singleton) return true;
             }
             if (source.flags & TypeFlags.Object && target.flags & TypeFlags.Object) {
                 const related = relation.get(getRelationKey(source, target, IntersectionState.None, relation));
@@ -17931,12 +17917,10 @@ namespace ts {
             }
 
             function isIdenticalTo(source: Type, target: Type): Ternary {
-                const flags = source.flags & target.flags;
-                if (!(flags & TypeFlags.Substructure)) {
-                    return Ternary.False;
-                }
+                if (source.flags !== target.flags) return Ternary.False;
+                if (source.flags & TypeFlags.Singleton) return Ternary.True;
                 traceUnionsOrIntersectionsTooLarge(source, target);
-                if (flags & TypeFlags.UnionOrIntersection) {
+                if (source.flags & TypeFlags.UnionOrIntersection) {
                     let result = eachTypeRelatedToSomeType(source as UnionOrIntersectionType, target as UnionOrIntersectionType);
                     if (result) {
                         result &= eachTypeRelatedToSomeType(target as UnionOrIntersectionType, source as UnionOrIntersectionType);
@@ -21131,7 +21115,6 @@ namespace ts {
             inferFromTypes(originalSource, originalTarget);
 
             function inferFromTypes(source: Type, target: Type): void {
-
                 if (!couldContainTypeVariables(target)) {
                     return;
                 }
@@ -21749,7 +21732,8 @@ namespace ts {
         }
 
         function isTypeOrBaseIdenticalTo(s: Type, t: Type) {
-            return isTypeIdenticalTo(s, t) || !!(t.flags & TypeFlags.String && s.flags & TypeFlags.StringLiteral || t.flags & TypeFlags.Number && s.flags & TypeFlags.NumberLiteral);
+            return strictOptionalProperties && t === missingType ? s === t :
+                (isTypeIdenticalTo(s, t) || !!(t.flags & TypeFlags.String && s.flags & TypeFlags.StringLiteral || t.flags & TypeFlags.Number && s.flags & TypeFlags.NumberLiteral));
         }
 
         function isTypeCloselyMatchedBy(s: Type, t: Type) {
diff --git a/src/compiler/types.ts b/src/compiler/types.ts
index 7df907413df06..90eadbdce5c82 100644
--- a/src/compiler/types.ts
+++ b/src/compiler/types.ts
@@ -5086,7 +5086,7 @@ namespace ts {
         /* @internal */
         Simplifiable = IndexedAccess | Conditional,
         /* @internal */
-        Substructure = Object | Union | Intersection | Index | IndexedAccess | Conditional | Substitution | TemplateLiteral | StringMapping,
+        Singleton = Any | Unknown | String | Number | Boolean | BigInt | ESSymbol | Void | Undefined | Null | Never | NonPrimitive,
         // 'Narrowable' types are types where narrowing actually narrows.
         // This *should* be every type other than null, undefined, void, and never
         Narrowable = Any | Unknown | StructuredOrInstantiable | StringLike | NumberLike | BigIntLike | BooleanLike | ESSymbol | UniqueESSymbol | NonPrimitive,
diff --git a/tests/baselines/reference/strictOptionalProperties1.errors.txt b/tests/baselines/reference/strictOptionalProperties1.errors.txt
index 9d6fd76f53431..f0a8d00038a63 100644
--- a/tests/baselines/reference/strictOptionalProperties1.errors.txt
+++ b/tests/baselines/reference/strictOptionalProperties1.errors.txt
@@ -182,4 +182,64 @@ tests/cases/compiler/strictOptionalProperties1.ts(119,5): error TS2411: Property
         ~~~
 !!! error TS2411: Property 'bar' of type 'string | undefined' is not assignable to string index type 'string'.
     }
+    
+    // Strict optional properties and inference
+    
+    declare let ox1: { p: string };
+    declare let ox2: { p: string | undefined };
+    declare let ox3: { p?: string };
+    declare let ox4: { p?: string | undefined };
+    
+    declare let tx1: [string];
+    declare let tx2: [string | undefined];
+    declare let tx3: [string?];
+    declare let tx4: [(string | undefined)?];
+    
+    declare function f11<T>(x: { p?: T }): T;
+    
+    f11(ox1);  // string
+    f11(ox2);  // string | undefined
+    f11(ox3);  // string
+    f11(ox4);  // string | undefined
+    
+    declare function f12<T>(x: [T?]): T;
+    
+    f12(tx1);  // string
+    f12(tx2);  // string | undefined
+    f12(tx3);  // string
+    f12(tx4);  // string | undefined
+    
+    declare function f13<T>(x: Partial<T>): T;
+    
+    f13(ox1);  // { p: string }
+    f13(ox2);  // { p: string | undefined }
+    f13(ox3);  // { p: string }
+    f13(ox4);  // { p: string | undefined }
+    
+    f13(tx1);  // [string]
+    f13(tx2);  // [string | undefined]
+    f13(tx3);  // [string]
+    f13(tx4);  // [string | undefined]
+    
+    // Repro from #44388
+    
+    type Undefinable<T> = T | undefined;
+    
+    function expectNotUndefined<T>(value: Undefinable<T>): T {
+        if (value === undefined) {
+            throw new TypeError('value is undefined');
+        }
+        return value;
+    }
+    
+    interface Bar {
+        bar?: number;
+    }
+    
+    function aa(input: Bar): void {
+        const notUndefinedVal = expectNotUndefined(input.bar);
+        bb(notUndefinedVal);
+    }
+    
+    declare function bb(input: number): void;
     
\ No newline at end of file
diff --git a/tests/baselines/reference/strictOptionalProperties1.js b/tests/baselines/reference/strictOptionalProperties1.js
index 028e43b9ca614..9f00711561343 100644
--- a/tests/baselines/reference/strictOptionalProperties1.js
+++ b/tests/baselines/reference/strictOptionalProperties1.js
@@ -119,6 +119,66 @@ interface Test {
     foo?: string;  // Should be ok
     bar?: string | undefined;  // Error
 }
+
+// Strict optional properties and inference
+
+declare let ox1: { p: string };
+declare let ox2: { p: string | undefined };
+declare let ox3: { p?: string };
+declare let ox4: { p?: string | undefined };
+
+declare let tx1: [string];
+declare let tx2: [string | undefined];
+declare let tx3: [string?];
+declare let tx4: [(string | undefined)?];
+
+declare function f11<T>(x: { p?: T }): T;
+
+f11(ox1);  // string
+f11(ox2);  // string | undefined
+f11(ox3);  // string
+f11(ox4);  // string | undefined
+
+declare function f12<T>(x: [T?]): T;
+
+f12(tx1);  // string
+f12(tx2);  // string | undefined
+f12(tx3);  // string
+f12(tx4);  // string | undefined
+
+declare function f13<T>(x: Partial<T>): T;
+
+f13(ox1);  // { p: string }
+f13(ox2);  // { p: string | undefined }
+f13(ox3);  // { p: string }
+f13(ox4);  // { p: string | undefined }
+
+f13(tx1);  // [string]
+f13(tx2);  // [string | undefined]
+f13(tx3);  // [string]
+f13(tx4);  // [string | undefined]
+
+// Repro from #44388
+
+type Undefinable<T> = T | undefined;
+
+function expectNotUndefined<T>(value: Undefinable<T>): T {
+    if (value === undefined) {
+        throw new TypeError('value is undefined');
+    }
+    return value;
+}
+
+interface Bar {
+    bar?: number;
+}
+
+function aa(input: Bar): void {
+    const notUndefinedVal = expectNotUndefined(input.bar);
+    bb(notUndefinedVal);
+}
+
+declare function bb(input: number): void;
 
 
 //// [strictOptionalProperties1.js]
@@ -223,6 +283,32 @@ var t4 = [1, undefined, undefined];
 // Example from #13195
 var x = { foo: undefined };
 var y = __assign({ foo: 123 }, x);
+f11(ox1); // string
+f11(ox2); // string | undefined
+f11(ox3); // string
+f11(ox4); // string | undefined
+f12(tx1); // string
+f12(tx2); // string | undefined
+f12(tx3); // string
+f12(tx4); // string | undefined
+f13(ox1); // { p: string }
+f13(ox2); // { p: string | undefined }
+f13(ox3); // { p: string }
+f13(ox4); // { p: string | undefined }
+f13(tx1); // [string]
+f13(tx2); // [string | undefined]
+f13(tx3); // [string]
+f13(tx4); // [string | undefined]
+function expectNotUndefined(value) {
+    if (value === undefined) {
+        throw new TypeError('value is undefined');
+    }
+    return value;
+}
+function aa(input) {
+    var notUndefinedVal = expectNotUndefined(input.bar);
+    bb(notUndefinedVal);
+}
 
 
 //// [strictOptionalProperties1.d.ts]
@@ -268,3 +354,31 @@ interface Test {
     foo?: string;
     bar?: string | undefined;
 }
+declare let ox1: {
+    p: string;
+};
+declare let ox2: {
+    p: string | undefined;
+};
+declare let ox3: {
+    p?: string;
+};
+declare let ox4: {
+    p?: string | undefined;
+};
+declare let tx1: [string];
+declare let tx2: [string | undefined];
+declare let tx3: [string?];
+declare let tx4: [(string | undefined)?];
+declare function f11<T>(x: {
+    p?: T;
+}): T;
+declare function f12<T>(x: [T?]): T;
+declare function f13<T>(x: Partial<T>): T;
+declare type Undefinable<T> = T | undefined;
+declare function expectNotUndefined<T>(value: Undefinable<T>): T;
+interface Bar {
+    bar?: number;
+}
+declare function aa(input: Bar): void;
+declare function bb(input: number): void;
diff --git a/tests/baselines/reference/strictOptionalProperties1.symbols b/tests/baselines/reference/strictOptionalProperties1.symbols
index 33caabc10f344..bfae149bdbef0 100644
--- a/tests/baselines/reference/strictOptionalProperties1.symbols
+++ b/tests/baselines/reference/strictOptionalProperties1.symbols
@@ -400,3 +400,174 @@ interface Test {
 >bar : Symbol(Test.bar, Decl(strictOptionalProperties1.ts, 117, 17))
 }
 
+// Strict optional properties and inference
+
+declare let ox1: { p: string };
+>ox1 : Symbol(ox1, Decl(strictOptionalProperties1.ts, 123, 11))
+>p : Symbol(p, Decl(strictOptionalProperties1.ts, 123, 18))
+
+declare let ox2: { p: string | undefined };
+>ox2 : Symbol(ox2, Decl(strictOptionalProperties1.ts, 124, 11))
+>p : Symbol(p, Decl(strictOptionalProperties1.ts, 124, 18))
+
+declare let ox3: { p?: string };
+>ox3 : Symbol(ox3, Decl(strictOptionalProperties1.ts, 125, 11))
+>p : Symbol(p, Decl(strictOptionalProperties1.ts, 125, 18))
+
+declare let ox4: { p?: string | undefined };
+>ox4 : Symbol(ox4, Decl(strictOptionalProperties1.ts, 126, 11))
+>p : Symbol(p, Decl(strictOptionalProperties1.ts, 126, 18))
+
+declare let tx1: [string];
+>tx1 : Symbol(tx1, Decl(strictOptionalProperties1.ts, 128, 11))
+
+declare let tx2: [string | undefined];
+>tx2 : Symbol(tx2, Decl(strictOptionalProperties1.ts, 129, 11))
+
+declare let tx3: [string?];
+>tx3 : Symbol(tx3, Decl(strictOptionalProperties1.ts, 130, 11))
+
+declare let tx4: [(string | undefined)?];
+>tx4 : Symbol(tx4, Decl(strictOptionalProperties1.ts, 131, 11))
+
+declare function f11<T>(x: { p?: T }): T;
+>f11 : Symbol(f11, Decl(strictOptionalProperties1.ts, 131, 41))
+>T : Symbol(T, Decl(strictOptionalProperties1.ts, 133, 21))
+>x : Symbol(x, Decl(strictOptionalProperties1.ts, 133, 24))
+>p : Symbol(p, Decl(strictOptionalProperties1.ts, 133, 28))
+>T : Symbol(T, Decl(strictOptionalProperties1.ts, 133, 21))
+>T : Symbol(T, Decl(strictOptionalProperties1.ts, 133, 21))
+
+f11(ox1);  // string
+>f11 : Symbol(f11, Decl(strictOptionalProperties1.ts, 131, 41))
+>ox1 : Symbol(ox1, Decl(strictOptionalProperties1.ts, 123, 11))
+
+f11(ox2);  // string | undefined
+>f11 : Symbol(f11, Decl(strictOptionalProperties1.ts, 131, 41))
+>ox2 : Symbol(ox2, Decl(strictOptionalProperties1.ts, 124, 11))
+
+f11(ox3);  // string
+>f11 : Symbol(f11, Decl(strictOptionalProperties1.ts, 131, 41))
+>ox3 : Symbol(ox3, Decl(strictOptionalProperties1.ts, 125, 11))
+
+f11(ox4);  // string | undefined
+>f11 : Symbol(f11, Decl(strictOptionalProperties1.ts, 131, 41))
+>ox4 : Symbol(ox4, Decl(strictOptionalProperties1.ts, 126, 11))
+
+declare function f12<T>(x: [T?]): T;
+>f12 : Symbol(f12, Decl(strictOptionalProperties1.ts, 138, 9))
+>T : Symbol(T, Decl(strictOptionalProperties1.ts, 140, 21))
+>x : Symbol(x, Decl(strictOptionalProperties1.ts, 140, 24))
+>T : Symbol(T, Decl(strictOptionalProperties1.ts, 140, 21))
+>T : Symbol(T, Decl(strictOptionalProperties1.ts, 140, 21))
+
+f12(tx1);  // string
+>f12 : Symbol(f12, Decl(strictOptionalProperties1.ts, 138, 9))
+>tx1 : Symbol(tx1, Decl(strictOptionalProperties1.ts, 128, 11))
+
+f12(tx2);  // string | undefined
+>f12 : Symbol(f12, Decl(strictOptionalProperties1.ts, 138, 9))
+>tx2 : Symbol(tx2, Decl(strictOptionalProperties1.ts, 129, 11))
+
+f12(tx3);  // string
+>f12 : Symbol(f12, Decl(strictOptionalProperties1.ts, 138, 9))
+>tx3 : Symbol(tx3, Decl(strictOptionalProperties1.ts, 130, 11))
+
+f12(tx4);  // string | undefined
+>f12 : Symbol(f12, Decl(strictOptionalProperties1.ts, 138, 9))
+>tx4 : Symbol(tx4, Decl(strictOptionalProperties1.ts, 131, 11))
+
+declare function f13<T>(x: Partial<T>): T;
+>f13 : Symbol(f13, Decl(strictOptionalProperties1.ts, 145, 9))
+>T : Symbol(T, Decl(strictOptionalProperties1.ts, 147, 21))
+>x : Symbol(x, Decl(strictOptionalProperties1.ts, 147, 24))
+>Partial : Symbol(Partial, Decl(lib.es5.d.ts, --, --))
+>T : Symbol(T, Decl(strictOptionalProperties1.ts, 147, 21))
+>T : Symbol(T, Decl(strictOptionalProperties1.ts, 147, 21))
+
+f13(ox1);  // { p: string }
+>f13 : Symbol(f13, Decl(strictOptionalProperties1.ts, 145, 9))
+>ox1 : Symbol(ox1, Decl(strictOptionalProperties1.ts, 123, 11))
+
+f13(ox2);  // { p: string | undefined }
+>f13 : Symbol(f13, Decl(strictOptionalProperties1.ts, 145, 9))
+>ox2 : Symbol(ox2, Decl(strictOptionalProperties1.ts, 124, 11))
+
+f13(ox3);  // { p: string }
+>f13 : Symbol(f13, Decl(strictOptionalProperties1.ts, 145, 9))
+>ox3 : Symbol(ox3, Decl(strictOptionalProperties1.ts, 125, 11))
+
+f13(ox4);  // { p: string | undefined }
+>f13 : Symbol(f13, Decl(strictOptionalProperties1.ts, 145, 9))
+>ox4 : Symbol(ox4, Decl(strictOptionalProperties1.ts, 126, 11))
+
+f13(tx1);  // [string]
+>f13 : Symbol(f13, Decl(strictOptionalProperties1.ts, 145, 9))
+>tx1 : Symbol(tx1, Decl(strictOptionalProperties1.ts, 128, 11))
+
+f13(tx2);  // [string | undefined]
+>f13 : Symbol(f13, Decl(strictOptionalProperties1.ts, 145, 9))
+>tx2 : Symbol(tx2, Decl(strictOptionalProperties1.ts, 129, 11))
+
+f13(tx3);  // [string]
+>f13 : Symbol(f13, Decl(strictOptionalProperties1.ts, 145, 9))
+>tx3 : Symbol(tx3, Decl(strictOptionalProperties1.ts, 130, 11))
+
+f13(tx4);  // [string | undefined]
+>f13 : Symbol(f13, Decl(strictOptionalProperties1.ts, 145, 9))
+>tx4 : Symbol(tx4, Decl(strictOptionalProperties1.ts, 131, 11))
+
+// Repro from #44388
+
+type Undefinable<T> = T | undefined;
+>Undefinable : Symbol(Undefinable, Decl(strictOptionalProperties1.ts, 157, 9))
+>T : Symbol(T, Decl(strictOptionalProperties1.ts, 161, 17))
+>T : Symbol(T, Decl(strictOptionalProperties1.ts, 161, 17))
+
+function expectNotUndefined<T>(value: Undefinable<T>): T {
+>expectNotUndefined : Symbol(expectNotUndefined, Decl(strictOptionalProperties1.ts, 161, 36))
+>T : Symbol(T, Decl(strictOptionalProperties1.ts, 163, 28))
+>value : Symbol(value, Decl(strictOptionalProperties1.ts, 163, 31))
+>Undefinable : Symbol(Undefinable, Decl(strictOptionalProperties1.ts, 157, 9))
+>T : Symbol(T, Decl(strictOptionalProperties1.ts, 163, 28))
+>T : Symbol(T, Decl(strictOptionalProperties1.ts, 163, 28))
+
+    if (value === undefined) {
+>value : Symbol(value, Decl(strictOptionalProperties1.ts, 163, 31))
+>undefined : Symbol(undefined)
+
+        throw new TypeError('value is undefined');
+>TypeError : Symbol(TypeError, Decl(lib.es5.d.ts, --, --), Decl(lib.es5.d.ts, --, --))
+    }
+    return value;
+>value : Symbol(value, Decl(strictOptionalProperties1.ts, 163, 31))
+}
+
+interface Bar {
+>Bar : Symbol(Bar, Decl(strictOptionalProperties1.ts, 168, 1))
+
+    bar?: number;
+>bar : Symbol(Bar.bar, Decl(strictOptionalProperties1.ts, 170, 15))
+}
+
+function aa(input: Bar): void {
+>aa : Symbol(aa, Decl(strictOptionalProperties1.ts, 172, 1))
+>input : Symbol(input, Decl(strictOptionalProperties1.ts, 174, 12))
+>Bar : Symbol(Bar, Decl(strictOptionalProperties1.ts, 168, 1))
+
+    const notUndefinedVal = expectNotUndefined(input.bar);
+>notUndefinedVal : Symbol(notUndefinedVal, Decl(strictOptionalProperties1.ts, 175, 9))
+>expectNotUndefined : Symbol(expectNotUndefined, Decl(strictOptionalProperties1.ts, 161, 36))
+>input.bar : Symbol(Bar.bar, Decl(strictOptionalProperties1.ts, 170, 15))
+>input : Symbol(input, Decl(strictOptionalProperties1.ts, 174, 12))
+>bar : Symbol(Bar.bar, Decl(strictOptionalProperties1.ts, 170, 15))
+
+    bb(notUndefinedVal);
+>bb : Symbol(bb, Decl(strictOptionalProperties1.ts, 177, 1))
+>notUndefinedVal : Symbol(notUndefinedVal, Decl(strictOptionalProperties1.ts, 175, 9))
+}
+
+declare function bb(input: number): void;
+>bb : Symbol(bb, Decl(strictOptionalProperties1.ts, 177, 1))
+>input : Symbol(input, Decl(strictOptionalProperties1.ts, 179, 20))
+
diff --git a/tests/baselines/reference/strictOptionalProperties1.types b/tests/baselines/reference/strictOptionalProperties1.types
index fd208b335d905..c59cbc5d269c2 100644
--- a/tests/baselines/reference/strictOptionalProperties1.types
+++ b/tests/baselines/reference/strictOptionalProperties1.types
@@ -510,3 +510,176 @@ interface Test {
 >bar : string | undefined
 }
 
+// Strict optional properties and inference
+
+declare let ox1: { p: string };
+>ox1 : { p: string; }
+>p : string
+
+declare let ox2: { p: string | undefined };
+>ox2 : { p: string | undefined; }
+>p : string | undefined
+
+declare let ox3: { p?: string };
+>ox3 : { p?: string; }
+>p : string | undefined
+
+declare let ox4: { p?: string | undefined };
+>ox4 : { p?: string | undefined; }
+>p : string | undefined
+
+declare let tx1: [string];
+>tx1 : [string]
+
+declare let tx2: [string | undefined];
+>tx2 : [string | undefined]
+
+declare let tx3: [string?];
+>tx3 : [string?]
+
+declare let tx4: [(string | undefined)?];
+>tx4 : [(string | undefined)?]
+
+declare function f11<T>(x: { p?: T }): T;
+>f11 : <T>(x: {    p?: T;}) => T
+>x : { p?: T; }
+>p : T | undefined
+
+f11(ox1);  // string
+>f11(ox1) : string
+>f11 : <T>(x: { p?: T; }) => T
+>ox1 : { p: string; }
+
+f11(ox2);  // string | undefined
+>f11(ox2) : string | undefined
+>f11 : <T>(x: { p?: T; }) => T
+>ox2 : { p: string | undefined; }
+
+f11(ox3);  // string
+>f11(ox3) : string
+>f11 : <T>(x: { p?: T; }) => T
+>ox3 : { p?: string; }
+
+f11(ox4);  // string | undefined
+>f11(ox4) : string | undefined
+>f11 : <T>(x: { p?: T; }) => T
+>ox4 : { p?: string | undefined; }
+
+declare function f12<T>(x: [T?]): T;
+>f12 : <T>(x: [T?]) => T
+>x : [T?]
+
+f12(tx1);  // string
+>f12(tx1) : string
+>f12 : <T>(x: [T?]) => T
+>tx1 : [string]
+
+f12(tx2);  // string | undefined
+>f12(tx2) : string | undefined
+>f12 : <T>(x: [T?]) => T
+>tx2 : [string | undefined]
+
+f12(tx3);  // string
+>f12(tx3) : string
+>f12 : <T>(x: [T?]) => T
+>tx3 : [string?]
+
+f12(tx4);  // string | undefined
+>f12(tx4) : string | undefined
+>f12 : <T>(x: [T?]) => T
+>tx4 : [(string | undefined)?]
+
+declare function f13<T>(x: Partial<T>): T;
+>f13 : <T>(x: Partial<T>) => T
+>x : Partial<T>
+
+f13(ox1);  // { p: string }
+>f13(ox1) : { p: string; }
+>f13 : <T>(x: Partial<T>) => T
+>ox1 : { p: string; }
+
+f13(ox2);  // { p: string | undefined }
+>f13(ox2) : { p: string | undefined; }
+>f13 : <T>(x: Partial<T>) => T
+>ox2 : { p: string | undefined; }
+
+f13(ox3);  // { p: string }
+>f13(ox3) : { p: string; }
+>f13 : <T>(x: Partial<T>) => T
+>ox3 : { p?: string; }
+
+f13(ox4);  // { p: string | undefined }
+>f13(ox4) : { p: string | undefined; }
+>f13 : <T>(x: Partial<T>) => T
+>ox4 : { p?: string | undefined; }
+
+f13(tx1);  // [string]
+>f13(tx1) : [string]
+>f13 : <T>(x: Partial<T>) => T
+>tx1 : [string]
+
+f13(tx2);  // [string | undefined]
+>f13(tx2) : [string | undefined]
+>f13 : <T>(x: Partial<T>) => T
+>tx2 : [string | undefined]
+
+f13(tx3);  // [string]
+>f13(tx3) : [string]
+>f13 : <T>(x: Partial<T>) => T
+>tx3 : [string?]
+
+f13(tx4);  // [string | undefined]
+>f13(tx4) : [string | undefined]
+>f13 : <T>(x: Partial<T>) => T
+>tx4 : [(string | undefined)?]
+
+// Repro from #44388
+
+type Undefinable<T> = T | undefined;
+>Undefinable : Undefinable<T>
+
+function expectNotUndefined<T>(value: Undefinable<T>): T {
+>expectNotUndefined : <T>(value: Undefinable<T>) => T
+>value : Undefinable<T>
+
+    if (value === undefined) {
+>value === undefined : boolean
+>value : Undefinable<T>
+>undefined : undefined
+
+        throw new TypeError('value is undefined');
+>new TypeError('value is undefined') : TypeError
+>TypeError : TypeErrorConstructor
+>'value is undefined' : "value is undefined"
+    }
+    return value;
+>value : T
+}
+
+interface Bar {
+    bar?: number;
+>bar : number | undefined
+}
+
+function aa(input: Bar): void {
+>aa : (input: Bar) => void
+>input : Bar
+
+    const notUndefinedVal = expectNotUndefined(input.bar);
+>notUndefinedVal : number
+>expectNotUndefined(input.bar) : number
+>expectNotUndefined : <T>(value: Undefinable<T>) => T
+>input.bar : number | undefined
+>input : Bar
+>bar : number | undefined
+
+    bb(notUndefinedVal);
+>bb(notUndefinedVal) : void
+>bb : (input: number) => void
+>notUndefinedVal : number
+}
+
+declare function bb(input: number): void;
+>bb : (input: number) => void
+>input : number
+
diff --git a/tests/cases/compiler/strictOptionalProperties1.ts b/tests/cases/compiler/strictOptionalProperties1.ts
index 3ebe9773af75a..fd47c98aad01d 100644
--- a/tests/cases/compiler/strictOptionalProperties1.ts
+++ b/tests/cases/compiler/strictOptionalProperties1.ts
@@ -121,3 +121,63 @@ interface Test {
     foo?: string;  // Should be ok
     bar?: string | undefined;  // Error
 }
+
+// Strict optional properties and inference
+
+declare let ox1: { p: string };
+declare let ox2: { p: string | undefined };
+declare let ox3: { p?: string };
+declare let ox4: { p?: string | undefined };
+
+declare let tx1: [string];
+declare let tx2: [string | undefined];
+declare let tx3: [string?];
+declare let tx4: [(string | undefined)?];
+
+declare function f11<T>(x: { p?: T }): T;
+
+f11(ox1);  // string
+f11(ox2);  // string | undefined
+f11(ox3);  // string
+f11(ox4);  // string | undefined
+
+declare function f12<T>(x: [T?]): T;
+
+f12(tx1);  // string
+f12(tx2);  // string | undefined
+f12(tx3);  // string
+f12(tx4);  // string | undefined
+
+declare function f13<T>(x: Partial<T>): T;
+
+f13(ox1);  // { p: string }
+f13(ox2);  // { p: string | undefined }
+f13(ox3);  // { p: string }
+f13(ox4);  // { p: string | undefined }
+
+f13(tx1);  // [string]
+f13(tx2);  // [string | undefined]
+f13(tx3);  // [string]
+f13(tx4);  // [string | undefined]
+
+// Repro from #44388
+
+type Undefinable<T> = T | undefined;
+
+function expectNotUndefined<T>(value: Undefinable<T>): T {
+    if (value === undefined) {
+        throw new TypeError('value is undefined');
+    }
+    return value;
+}
+
+interface Bar {
+    bar?: number;
+}
+
+function aa(input: Bar): void {
+    const notUndefinedVal = expectNotUndefined(input.bar);
+    bb(notUndefinedVal);
+}
+
+declare function bb(input: number): void;