diff --git a/src/compiler/checker.ts b/src/compiler/checker.ts
index d825b0d971758..dfb1a4c8c4e89 100644
--- a/src/compiler/checker.ts
+++ b/src/compiler/checker.ts
@@ -10716,19 +10716,18 @@ namespace ts {
                             return result;
                         }
                     }
-                    let constraint = getConstraintForRelation(<TypeParameter>source);
-                    // A type variable with no constraint is not related to the non-primitive object type.
-                    if (constraint || !(target.flags & TypeFlags.NonPrimitive)) {
-                        if (!constraint || constraint.flags & TypeFlags.Any) {
-                            constraint = emptyObjectType;
-                        }
-                        // Report constraint errors only if the constraint is not the empty object type
-                        const reportConstraintErrors = reportErrors && constraint !== emptyObjectType;
-                        if (result = isRelatedTo(constraint, target, reportConstraintErrors)) {
+                    const constraint = getConstraintForRelation(<TypeParameter>source);
+                    if (!constraint || constraint.flags & TypeFlags.Any) {
+                        // A type variable with no constraint is not related to the non-primitive object type.
+                        if (result = isRelatedTo(emptyObjectType, extractTypesOfKind(target, ~TypeFlags.NonPrimitive))) {
                             errorInfo = saveErrorInfo;
                             return result;
                         }
                     }
+                    else if (result = isRelatedTo(constraint, target, reportErrors)) {
+                        errorInfo = saveErrorInfo;
+                        return result;
+                    }
                 }
                 else if (source.flags & TypeFlags.Index) {
                     if (result = isRelatedTo(keyofConstraintType, target, reportErrors)) {
diff --git a/tests/baselines/reference/nonPrimitiveAndTypeVariables.errors.txt b/tests/baselines/reference/nonPrimitiveAndTypeVariables.errors.txt
new file mode 100644
index 0000000000000..83ce98f1cd625
--- /dev/null
+++ b/tests/baselines/reference/nonPrimitiveAndTypeVariables.errors.txt
@@ -0,0 +1,24 @@
+tests/cases/conformance/types/nonPrimitive/nonPrimitiveAndTypeVariables.ts(10,9): error TS2322: Type 'T' is not assignable to type 'object'.
+tests/cases/conformance/types/nonPrimitive/nonPrimitiveAndTypeVariables.ts(11,9): error TS2322: Type 'T' is not assignable to type 'object | U'.
+  Type 'T' is not assignable to type 'U'.
+
+
+==== tests/cases/conformance/types/nonPrimitive/nonPrimitiveAndTypeVariables.ts (2 errors) ====
+    // Repros from #23800
+    
+    type A<T, V> = { [P in keyof T]: T[P] extends V ? 1 : 0; };
+    type B<T, V> = { [P in keyof T]: T[P] extends V | object ? 1 : 0; };
+    
+    let a: A<{ a: 0 | 1 }, 0> = { a: 0 };
+    let b: B<{ a: 0 | 1 }, 0> = { a: 0 };
+    
+    function foo<T, U>(x: T) {
+        let a: object = x;  // Error
+            ~
+!!! error TS2322: Type 'T' is not assignable to type 'object'.
+        let b: U | object = x;  // Error
+            ~
+!!! error TS2322: Type 'T' is not assignable to type 'object | U'.
+!!! error TS2322:   Type 'T' is not assignable to type 'U'.
+    }
+    
\ No newline at end of file
diff --git a/tests/baselines/reference/nonPrimitiveAndTypeVariables.js b/tests/baselines/reference/nonPrimitiveAndTypeVariables.js
new file mode 100644
index 0000000000000..fda272c1fe26d
--- /dev/null
+++ b/tests/baselines/reference/nonPrimitiveAndTypeVariables.js
@@ -0,0 +1,24 @@
+//// [nonPrimitiveAndTypeVariables.ts]
+// Repros from #23800
+
+type A<T, V> = { [P in keyof T]: T[P] extends V ? 1 : 0; };
+type B<T, V> = { [P in keyof T]: T[P] extends V | object ? 1 : 0; };
+
+let a: A<{ a: 0 | 1 }, 0> = { a: 0 };
+let b: B<{ a: 0 | 1 }, 0> = { a: 0 };
+
+function foo<T, U>(x: T) {
+    let a: object = x;  // Error
+    let b: U | object = x;  // Error
+}
+
+
+//// [nonPrimitiveAndTypeVariables.js]
+"use strict";
+// Repros from #23800
+var a = { a: 0 };
+var b = { a: 0 };
+function foo(x) {
+    var a = x; // Error
+    var b = x; // Error
+}
diff --git a/tests/baselines/reference/nonPrimitiveAndTypeVariables.symbols b/tests/baselines/reference/nonPrimitiveAndTypeVariables.symbols
new file mode 100644
index 0000000000000..083c67e7fdb23
--- /dev/null
+++ b/tests/baselines/reference/nonPrimitiveAndTypeVariables.symbols
@@ -0,0 +1,52 @@
+=== tests/cases/conformance/types/nonPrimitive/nonPrimitiveAndTypeVariables.ts ===
+// Repros from #23800
+
+type A<T, V> = { [P in keyof T]: T[P] extends V ? 1 : 0; };
+>A : Symbol(A, Decl(nonPrimitiveAndTypeVariables.ts, 0, 0))
+>T : Symbol(T, Decl(nonPrimitiveAndTypeVariables.ts, 2, 7))
+>V : Symbol(V, Decl(nonPrimitiveAndTypeVariables.ts, 2, 9))
+>P : Symbol(P, Decl(nonPrimitiveAndTypeVariables.ts, 2, 18))
+>T : Symbol(T, Decl(nonPrimitiveAndTypeVariables.ts, 2, 7))
+>T : Symbol(T, Decl(nonPrimitiveAndTypeVariables.ts, 2, 7))
+>P : Symbol(P, Decl(nonPrimitiveAndTypeVariables.ts, 2, 18))
+>V : Symbol(V, Decl(nonPrimitiveAndTypeVariables.ts, 2, 9))
+
+type B<T, V> = { [P in keyof T]: T[P] extends V | object ? 1 : 0; };
+>B : Symbol(B, Decl(nonPrimitiveAndTypeVariables.ts, 2, 59))
+>T : Symbol(T, Decl(nonPrimitiveAndTypeVariables.ts, 3, 7))
+>V : Symbol(V, Decl(nonPrimitiveAndTypeVariables.ts, 3, 9))
+>P : Symbol(P, Decl(nonPrimitiveAndTypeVariables.ts, 3, 18))
+>T : Symbol(T, Decl(nonPrimitiveAndTypeVariables.ts, 3, 7))
+>T : Symbol(T, Decl(nonPrimitiveAndTypeVariables.ts, 3, 7))
+>P : Symbol(P, Decl(nonPrimitiveAndTypeVariables.ts, 3, 18))
+>V : Symbol(V, Decl(nonPrimitiveAndTypeVariables.ts, 3, 9))
+
+let a: A<{ a: 0 | 1 }, 0> = { a: 0 };
+>a : Symbol(a, Decl(nonPrimitiveAndTypeVariables.ts, 5, 3))
+>A : Symbol(A, Decl(nonPrimitiveAndTypeVariables.ts, 0, 0))
+>a : Symbol(a, Decl(nonPrimitiveAndTypeVariables.ts, 5, 10))
+>a : Symbol(a, Decl(nonPrimitiveAndTypeVariables.ts, 5, 29))
+
+let b: B<{ a: 0 | 1 }, 0> = { a: 0 };
+>b : Symbol(b, Decl(nonPrimitiveAndTypeVariables.ts, 6, 3))
+>B : Symbol(B, Decl(nonPrimitiveAndTypeVariables.ts, 2, 59))
+>a : Symbol(a, Decl(nonPrimitiveAndTypeVariables.ts, 6, 10))
+>a : Symbol(a, Decl(nonPrimitiveAndTypeVariables.ts, 6, 29))
+
+function foo<T, U>(x: T) {
+>foo : Symbol(foo, Decl(nonPrimitiveAndTypeVariables.ts, 6, 37))
+>T : Symbol(T, Decl(nonPrimitiveAndTypeVariables.ts, 8, 13))
+>U : Symbol(U, Decl(nonPrimitiveAndTypeVariables.ts, 8, 15))
+>x : Symbol(x, Decl(nonPrimitiveAndTypeVariables.ts, 8, 19))
+>T : Symbol(T, Decl(nonPrimitiveAndTypeVariables.ts, 8, 13))
+
+    let a: object = x;  // Error
+>a : Symbol(a, Decl(nonPrimitiveAndTypeVariables.ts, 9, 7))
+>x : Symbol(x, Decl(nonPrimitiveAndTypeVariables.ts, 8, 19))
+
+    let b: U | object = x;  // Error
+>b : Symbol(b, Decl(nonPrimitiveAndTypeVariables.ts, 10, 7))
+>U : Symbol(U, Decl(nonPrimitiveAndTypeVariables.ts, 8, 15))
+>x : Symbol(x, Decl(nonPrimitiveAndTypeVariables.ts, 8, 19))
+}
+
diff --git a/tests/baselines/reference/nonPrimitiveAndTypeVariables.types b/tests/baselines/reference/nonPrimitiveAndTypeVariables.types
new file mode 100644
index 0000000000000..f2fba1201407f
--- /dev/null
+++ b/tests/baselines/reference/nonPrimitiveAndTypeVariables.types
@@ -0,0 +1,56 @@
+=== tests/cases/conformance/types/nonPrimitive/nonPrimitiveAndTypeVariables.ts ===
+// Repros from #23800
+
+type A<T, V> = { [P in keyof T]: T[P] extends V ? 1 : 0; };
+>A : A<T, V>
+>T : T
+>V : V
+>P : P
+>T : T
+>T : T
+>P : P
+>V : V
+
+type B<T, V> = { [P in keyof T]: T[P] extends V | object ? 1 : 0; };
+>B : B<T, V>
+>T : T
+>V : V
+>P : P
+>T : T
+>T : T
+>P : P
+>V : V
+
+let a: A<{ a: 0 | 1 }, 0> = { a: 0 };
+>a : A<{ a: 0 | 1; }, 0>
+>A : A<T, V>
+>a : 0 | 1
+>{ a: 0 } : { a: 0; }
+>a : 0
+>0 : 0
+
+let b: B<{ a: 0 | 1 }, 0> = { a: 0 };
+>b : B<{ a: 0 | 1; }, 0>
+>B : B<T, V>
+>a : 0 | 1
+>{ a: 0 } : { a: 0; }
+>a : 0
+>0 : 0
+
+function foo<T, U>(x: T) {
+>foo : <T, U>(x: T) => void
+>T : T
+>U : U
+>x : T
+>T : T
+
+    let a: object = x;  // Error
+>a : object
+>x : T
+
+    let b: U | object = x;  // Error
+>b : object | U
+>U : U
+>x : T
+}
+
diff --git a/tests/cases/conformance/types/nonPrimitive/nonPrimitiveAndTypeVariables.ts b/tests/cases/conformance/types/nonPrimitive/nonPrimitiveAndTypeVariables.ts
new file mode 100644
index 0000000000000..a0eeec2cdd762
--- /dev/null
+++ b/tests/cases/conformance/types/nonPrimitive/nonPrimitiveAndTypeVariables.ts
@@ -0,0 +1,14 @@
+// @strict: true
+
+// Repros from #23800
+
+type A<T, V> = { [P in keyof T]: T[P] extends V ? 1 : 0; };
+type B<T, V> = { [P in keyof T]: T[P] extends V | object ? 1 : 0; };
+
+let a: A<{ a: 0 | 1 }, 0> = { a: 0 };
+let b: B<{ a: 0 | 1 }, 0> = { a: 0 };
+
+function foo<T, U>(x: T) {
+    let a: object = x;  // Error
+    let b: U | object = x;  // Error
+}