diff --git a/src/compiler/checker.ts b/src/compiler/checker.ts
index 23c5568f2e5f4..c9d20bdf1955d 100644
--- a/src/compiler/checker.ts
+++ b/src/compiler/checker.ts
@@ -17531,7 +17531,7 @@ namespace ts {
         // be "pushed" onto a node using the contextualType property.
         function getApparentTypeOfContextualType(node: Expression): Type | undefined {
             let contextualType = getContextualType(node);
-            contextualType = contextualType && mapType(contextualType, getApparentType);
+            contextualType = contextualType && mapType(contextualType, getApparentType, /*noReductions*/ true);
             if (contextualType && contextualType.flags & TypeFlags.Union) {
                 if (isObjectLiteralExpression(node)) {
                     return discriminateContextualTypeByObjectMembers(node, contextualType as UnionType);
diff --git a/tests/baselines/reference/contextualTypeShouldBeLiteral.js b/tests/baselines/reference/contextualTypeShouldBeLiteral.js
index dcb9da993c1cb..77bd62d10f844 100644
--- a/tests/baselines/reference/contextualTypeShouldBeLiteral.js
+++ b/tests/baselines/reference/contextualTypeShouldBeLiteral.js
@@ -93,7 +93,34 @@ let xyz: LikeA | LikeB = {
     }
 };
 
-xyz;
+xyz;
+
+// Repro: #29168
+
+interface TestObject {
+  type?: 'object';
+  items: {
+    [k: string]: TestGeneric;
+  };
+}
+
+interface TestString {
+  type: 'string';
+}
+
+type TestGeneric = (TestString | TestObject) & { [k: string]: any; };
+
+const testObj: TestGeneric = {
+  items: {
+    hello: { type: 'string' },
+    world: {
+      items: {
+        nested: { type: 'string' }
+      }
+    }
+  }
+};
+
 
 //// [contextualTypeShouldBeLiteral.js]
 "use strict";
@@ -134,3 +161,13 @@ var xyz = {
     }
 };
 xyz;
+var testObj = {
+    items: {
+        hello: { type: 'string' },
+        world: {
+            items: {
+                nested: { type: 'string' }
+            }
+        }
+    }
+};
diff --git a/tests/baselines/reference/contextualTypeShouldBeLiteral.symbols b/tests/baselines/reference/contextualTypeShouldBeLiteral.symbols
index 314117b509d94..156339e29b9a1 100644
--- a/tests/baselines/reference/contextualTypeShouldBeLiteral.symbols
+++ b/tests/baselines/reference/contextualTypeShouldBeLiteral.symbols
@@ -227,3 +227,59 @@ let xyz: LikeA | LikeB = {
 xyz;
 >xyz : Symbol(xyz, Decl(contextualTypeShouldBeLiteral.ts, 82, 3))
 
+// Repro: #29168
+
+interface TestObject {
+>TestObject : Symbol(TestObject, Decl(contextualTypeShouldBeLiteral.ts, 94, 4))
+
+  type?: 'object';
+>type : Symbol(TestObject.type, Decl(contextualTypeShouldBeLiteral.ts, 98, 22))
+
+  items: {
+>items : Symbol(TestObject.items, Decl(contextualTypeShouldBeLiteral.ts, 99, 18))
+
+    [k: string]: TestGeneric;
+>k : Symbol(k, Decl(contextualTypeShouldBeLiteral.ts, 101, 5))
+>TestGeneric : Symbol(TestGeneric, Decl(contextualTypeShouldBeLiteral.ts, 107, 1))
+
+  };
+}
+
+interface TestString {
+>TestString : Symbol(TestString, Decl(contextualTypeShouldBeLiteral.ts, 103, 1))
+
+  type: 'string';
+>type : Symbol(TestString.type, Decl(contextualTypeShouldBeLiteral.ts, 105, 22))
+}
+
+type TestGeneric = (TestString | TestObject) & { [k: string]: any; };
+>TestGeneric : Symbol(TestGeneric, Decl(contextualTypeShouldBeLiteral.ts, 107, 1))
+>TestString : Symbol(TestString, Decl(contextualTypeShouldBeLiteral.ts, 103, 1))
+>TestObject : Symbol(TestObject, Decl(contextualTypeShouldBeLiteral.ts, 94, 4))
+>k : Symbol(k, Decl(contextualTypeShouldBeLiteral.ts, 109, 50))
+
+const testObj: TestGeneric = {
+>testObj : Symbol(testObj, Decl(contextualTypeShouldBeLiteral.ts, 111, 5))
+>TestGeneric : Symbol(TestGeneric, Decl(contextualTypeShouldBeLiteral.ts, 107, 1))
+
+  items: {
+>items : Symbol(items, Decl(contextualTypeShouldBeLiteral.ts, 111, 30))
+
+    hello: { type: 'string' },
+>hello : Symbol(hello, Decl(contextualTypeShouldBeLiteral.ts, 112, 10))
+>type : Symbol(type, Decl(contextualTypeShouldBeLiteral.ts, 113, 12))
+
+    world: {
+>world : Symbol(world, Decl(contextualTypeShouldBeLiteral.ts, 113, 30))
+
+      items: {
+>items : Symbol(items, Decl(contextualTypeShouldBeLiteral.ts, 114, 12))
+
+        nested: { type: 'string' }
+>nested : Symbol(nested, Decl(contextualTypeShouldBeLiteral.ts, 115, 14))
+>type : Symbol(type, Decl(contextualTypeShouldBeLiteral.ts, 116, 17))
+      }
+    }
+  }
+};
+
diff --git a/tests/baselines/reference/contextualTypeShouldBeLiteral.types b/tests/baselines/reference/contextualTypeShouldBeLiteral.types
index a5867f0de42dc..a3814f499033b 100644
--- a/tests/baselines/reference/contextualTypeShouldBeLiteral.types
+++ b/tests/baselines/reference/contextualTypeShouldBeLiteral.types
@@ -222,3 +222,59 @@ let xyz: LikeA | LikeB = {
 xyz;
 >xyz : LikeA
 
+// Repro: #29168
+
+interface TestObject {
+  type?: 'object';
+>type : "object" | undefined
+
+  items: {
+>items : { [k: string]: TestGeneric; }
+
+    [k: string]: TestGeneric;
+>k : string
+
+  };
+}
+
+interface TestString {
+  type: 'string';
+>type : "string"
+}
+
+type TestGeneric = (TestString | TestObject) & { [k: string]: any; };
+>TestGeneric : TestGeneric
+>k : string
+
+const testObj: TestGeneric = {
+>testObj : TestGeneric
+>{  items: {    hello: { type: 'string' },    world: {      items: {        nested: { type: 'string' }      }    }  }} : { items: { hello: { type: "string"; }; world: { items: { nested: { type: "string"; }; }; }; }; }
+
+  items: {
+>items : { hello: { type: "string"; }; world: { items: { nested: { type: "string"; }; }; }; }
+>{    hello: { type: 'string' },    world: {      items: {        nested: { type: 'string' }      }    }  } : { hello: { type: "string"; }; world: { items: { nested: { type: "string"; }; }; }; }
+
+    hello: { type: 'string' },
+>hello : { type: "string"; }
+>{ type: 'string' } : { type: "string"; }
+>type : "string"
+>'string' : "string"
+
+    world: {
+>world : { items: { nested: { type: "string"; }; }; }
+>{      items: {        nested: { type: 'string' }      }    } : { items: { nested: { type: "string"; }; }; }
+
+      items: {
+>items : { nested: { type: "string"; }; }
+>{        nested: { type: 'string' }      } : { nested: { type: "string"; }; }
+
+        nested: { type: 'string' }
+>nested : { type: "string"; }
+>{ type: 'string' } : { type: "string"; }
+>type : "string"
+>'string' : "string"
+      }
+    }
+  }
+};
+
diff --git a/tests/baselines/reference/objectLiteralExcessProperties.errors.txt b/tests/baselines/reference/objectLiteralExcessProperties.errors.txt
index 4b034b06206df..e4fc4d69fca99 100644
--- a/tests/baselines/reference/objectLiteralExcessProperties.errors.txt
+++ b/tests/baselines/reference/objectLiteralExcessProperties.errors.txt
@@ -25,7 +25,7 @@ tests/cases/compiler/objectLiteralExcessProperties.ts(37,25): error TS2304: Cann
 tests/cases/compiler/objectLiteralExcessProperties.ts(39,11): error TS2322: Type '{ name: string; }' is not assignable to type 'T'.
 tests/cases/compiler/objectLiteralExcessProperties.ts(41,11): error TS2322: Type '{ name: string; prop: boolean; }' is not assignable to type 'T & { prop: boolean; }'.
   Type '{ name: string; prop: boolean; }' is not assignable to type 'T'.
-tests/cases/compiler/objectLiteralExcessProperties.ts(43,43): error TS2322: Type '{ name: string; prop: boolean; }' is not assignable to type 'T | { prop: boolean; }'.
+tests/cases/compiler/objectLiteralExcessProperties.ts(43,43): error TS2322: Type '{ name: string; prop: true; }' is not assignable to type 'T | { prop: boolean; }'.
   Object literal may only specify known properties, and 'name' does not exist in type '{ prop: boolean; }'.
 tests/cases/compiler/objectLiteralExcessProperties.ts(45,76): error TS2322: Type '{ name: string; prop: boolean; }' is not assignable to type '{ name: string; } | (T & { prop: boolean; })'.
   Object literal may only specify known properties, and 'prop' does not exist in type '{ name: string; }'.
@@ -119,7 +119,7 @@ tests/cases/compiler/objectLiteralExcessProperties.ts(49,44): error TS2322: Type
         // Excess property checks only on non-generic parts of unions
         const obj3: T | { prop: boolean } = { name: "test", prop: true };
                                               ~~~~~~~~~~~~
-!!! error TS2322: Type '{ name: string; prop: boolean; }' is not assignable to type 'T | { prop: boolean; }'.
+!!! error TS2322: Type '{ name: string; prop: true; }' is not assignable to type 'T | { prop: boolean; }'.
 !!! error TS2322:   Object literal may only specify known properties, and 'name' does not exist in type '{ prop: boolean; }'.
         // Excess property checks only on non-generic parts of unions
         const obj4: T & { prop: boolean } | { name: string } = { name: "test", prop: true };
diff --git a/tests/baselines/reference/objectLiteralExcessProperties.types b/tests/baselines/reference/objectLiteralExcessProperties.types
index 8765432ab7040..812f48c89048c 100644
--- a/tests/baselines/reference/objectLiteralExcessProperties.types
+++ b/tests/baselines/reference/objectLiteralExcessProperties.types
@@ -124,10 +124,10 @@ function test<T extends IFoo>() {
     const obj3: T | { prop: boolean } = { name: "test", prop: true };
 >obj3 : T | { prop: boolean; }
 >prop : boolean
->{ name: "test", prop: true } : { name: string; prop: boolean; }
+>{ name: "test", prop: true } : { name: string; prop: true; }
 >name : string
 >"test" : "test"
->prop : boolean
+>prop : true
 >true : true
 
     // Excess property checks only on non-generic parts of unions
diff --git a/tests/cases/compiler/contextualTypeShouldBeLiteral.ts b/tests/cases/compiler/contextualTypeShouldBeLiteral.ts
index 1012c567a71b5..a73ab5143d894 100644
--- a/tests/cases/compiler/contextualTypeShouldBeLiteral.ts
+++ b/tests/cases/compiler/contextualTypeShouldBeLiteral.ts
@@ -93,4 +93,30 @@ let xyz: LikeA | LikeB = {
     }
 };
 
-xyz;
\ No newline at end of file
+xyz;
+
+// Repro: #29168
+
+interface TestObject {
+  type?: 'object';
+  items: {
+    [k: string]: TestGeneric;
+  };
+}
+
+interface TestString {
+  type: 'string';
+}
+
+type TestGeneric = (TestString | TestObject) & { [k: string]: any; };
+
+const testObj: TestGeneric = {
+  items: {
+    hello: { type: 'string' },
+    world: {
+      items: {
+        nested: { type: 'string' }
+      }
+    }
+  }
+};