diff --git a/tests/baselines/reference/conditionalTypes2.errors.txt b/tests/baselines/reference/conditionalTypes2.errors.txt
index 0e7844babc6..c0c4211174c 100644
--- a/tests/baselines/reference/conditionalTypes2.errors.txt
+++ b/tests/baselines/reference/conditionalTypes2.errors.txt
@@ -191,4 +191,15 @@ tests/cases/conformance/types/conditional/conditionalTypes2.ts(75,12): error TS2
     
     type C<T, V, E> =
       { [Q in { [P in keyof T]: T[P] extends V ? P : P; }[keyof T]]: C<T[Q], V, E>; };
+    
+    // Repro from #23100
+    
+    type A2<T, V, E> =
+        T extends object ? T extends any[] ? T : { [Q in keyof T]: A2<T[Q], V, E>; } : T;
+    
+    type B2<T, V> =
+        T extends object ? T extends any[] ? T : { [Q in keyof T]: B2<T[Q], V>; } : T;
+    
+    type C2<T, V, E> =
+        T extends object ? { [Q in keyof T]: C2<T[Q], V, E>; } : T;
     
\ No newline at end of file
diff --git a/tests/baselines/reference/conditionalTypes2.js b/tests/baselines/reference/conditionalTypes2.js
index 7afb39d42bb..1f95e7eb8d9 100644
--- a/tests/baselines/reference/conditionalTypes2.js
+++ b/tests/baselines/reference/conditionalTypes2.js
@@ -134,6 +134,17 @@ type B<T, V> =
 
 type C<T, V, E> =
   { [Q in { [P in keyof T]: T[P] extends V ? P : P; }[keyof T]]: C<T[Q], V, E>; };
+
+// Repro from #23100
+
+type A2<T, V, E> =
+    T extends object ? T extends any[] ? T : { [Q in keyof T]: A2<T[Q], V, E>; } : T;
+
+type B2<T, V> =
+    T extends object ? T extends any[] ? T : { [Q in keyof T]: B2<T[Q], V>; } : T;
+
+type C2<T, V, E> =
+    T extends object ? { [Q in keyof T]: C2<T[Q], V, E>; } : T;
 
 
 //// [conditionalTypes2.js]
@@ -284,3 +295,12 @@ declare type C<T, V, E> = {
         [P in keyof T]: T[P] extends V ? P : P;
     }[keyof T]]: C<T[Q], V, E>;
 };
+declare type A2<T, V, E> = T extends object ? T extends any[] ? T : {
+    [Q in keyof T]: A2<T[Q], V, E>;
+} : T;
+declare type B2<T, V> = T extends object ? T extends any[] ? T : {
+    [Q in keyof T]: B2<T[Q], V>;
+} : T;
+declare type C2<T, V, E> = T extends object ? {
+    [Q in keyof T]: C2<T[Q], V, E>;
+} : T;
diff --git a/tests/baselines/reference/conditionalTypes2.symbols b/tests/baselines/reference/conditionalTypes2.symbols
index 00509458253..fb03b868a1d 100644
--- a/tests/baselines/reference/conditionalTypes2.symbols
+++ b/tests/baselines/reference/conditionalTypes2.symbols
@@ -496,3 +496,58 @@ type C<T, V, E> =
 >V : Symbol(V, Decl(conditionalTypes2.ts, 133, 9))
 >E : Symbol(E, Decl(conditionalTypes2.ts, 133, 12))
 
+// Repro from #23100
+
+type A2<T, V, E> =
+>A2 : Symbol(A2, Decl(conditionalTypes2.ts, 134, 82))
+>T : Symbol(T, Decl(conditionalTypes2.ts, 138, 8))
+>V : Symbol(V, Decl(conditionalTypes2.ts, 138, 10))
+>E : Symbol(E, Decl(conditionalTypes2.ts, 138, 13))
+
+    T extends object ? T extends any[] ? T : { [Q in keyof T]: A2<T[Q], V, E>; } : T;
+>T : Symbol(T, Decl(conditionalTypes2.ts, 138, 8))
+>T : Symbol(T, Decl(conditionalTypes2.ts, 138, 8))
+>T : Symbol(T, Decl(conditionalTypes2.ts, 138, 8))
+>Q : Symbol(Q, Decl(conditionalTypes2.ts, 139, 48))
+>T : Symbol(T, Decl(conditionalTypes2.ts, 138, 8))
+>A2 : Symbol(A2, Decl(conditionalTypes2.ts, 134, 82))
+>T : Symbol(T, Decl(conditionalTypes2.ts, 138, 8))
+>Q : Symbol(Q, Decl(conditionalTypes2.ts, 139, 48))
+>V : Symbol(V, Decl(conditionalTypes2.ts, 138, 10))
+>E : Symbol(E, Decl(conditionalTypes2.ts, 138, 13))
+>T : Symbol(T, Decl(conditionalTypes2.ts, 138, 8))
+
+type B2<T, V> =
+>B2 : Symbol(B2, Decl(conditionalTypes2.ts, 139, 85))
+>T : Symbol(T, Decl(conditionalTypes2.ts, 141, 8))
+>V : Symbol(V, Decl(conditionalTypes2.ts, 141, 10))
+
+    T extends object ? T extends any[] ? T : { [Q in keyof T]: B2<T[Q], V>; } : T;
+>T : Symbol(T, Decl(conditionalTypes2.ts, 141, 8))
+>T : Symbol(T, Decl(conditionalTypes2.ts, 141, 8))
+>T : Symbol(T, Decl(conditionalTypes2.ts, 141, 8))
+>Q : Symbol(Q, Decl(conditionalTypes2.ts, 142, 48))
+>T : Symbol(T, Decl(conditionalTypes2.ts, 141, 8))
+>B2 : Symbol(B2, Decl(conditionalTypes2.ts, 139, 85))
+>T : Symbol(T, Decl(conditionalTypes2.ts, 141, 8))
+>Q : Symbol(Q, Decl(conditionalTypes2.ts, 142, 48))
+>V : Symbol(V, Decl(conditionalTypes2.ts, 141, 10))
+>T : Symbol(T, Decl(conditionalTypes2.ts, 141, 8))
+
+type C2<T, V, E> =
+>C2 : Symbol(C2, Decl(conditionalTypes2.ts, 142, 82))
+>T : Symbol(T, Decl(conditionalTypes2.ts, 144, 8))
+>V : Symbol(V, Decl(conditionalTypes2.ts, 144, 10))
+>E : Symbol(E, Decl(conditionalTypes2.ts, 144, 13))
+
+    T extends object ? { [Q in keyof T]: C2<T[Q], V, E>; } : T;
+>T : Symbol(T, Decl(conditionalTypes2.ts, 144, 8))
+>Q : Symbol(Q, Decl(conditionalTypes2.ts, 145, 26))
+>T : Symbol(T, Decl(conditionalTypes2.ts, 144, 8))
+>C2 : Symbol(C2, Decl(conditionalTypes2.ts, 142, 82))
+>T : Symbol(T, Decl(conditionalTypes2.ts, 144, 8))
+>Q : Symbol(Q, Decl(conditionalTypes2.ts, 145, 26))
+>V : Symbol(V, Decl(conditionalTypes2.ts, 144, 10))
+>E : Symbol(E, Decl(conditionalTypes2.ts, 144, 13))
+>T : Symbol(T, Decl(conditionalTypes2.ts, 144, 8))
+
diff --git a/tests/baselines/reference/conditionalTypes2.types b/tests/baselines/reference/conditionalTypes2.types
index 5af4de235c8..906bc7e27df 100644
--- a/tests/baselines/reference/conditionalTypes2.types
+++ b/tests/baselines/reference/conditionalTypes2.types
@@ -526,3 +526,58 @@ type C<T, V, E> =
 >V : V
 >E : E
 
+// Repro from #23100
+
+type A2<T, V, E> =
+>A2 : A2<T, V, E>
+>T : T
+>V : V
+>E : E
+
+    T extends object ? T extends any[] ? T : { [Q in keyof T]: A2<T[Q], V, E>; } : T;
+>T : T
+>T : T
+>T : T
+>Q : Q
+>T : T
+>A2 : A2<T, V, E>
+>T : T
+>Q : Q
+>V : V
+>E : E
+>T : T
+
+type B2<T, V> =
+>B2 : B2<T, V>
+>T : T
+>V : V
+
+    T extends object ? T extends any[] ? T : { [Q in keyof T]: B2<T[Q], V>; } : T;
+>T : T
+>T : T
+>T : T
+>Q : Q
+>T : T
+>B2 : B2<T, V>
+>T : T
+>Q : Q
+>V : V
+>T : T
+
+type C2<T, V, E> =
+>C2 : C2<T, V, E>
+>T : T
+>V : V
+>E : E
+
+    T extends object ? { [Q in keyof T]: C2<T[Q], V, E>; } : T;
+>T : T
+>Q : Q
+>T : T
+>C2 : C2<T, V, E>
+>T : T
+>Q : Q
+>V : V
+>E : E
+>T : T
+