diff --git a/clang/lib/AST/Interp/ByteCodeExprGen.cpp b/clang/lib/AST/Interp/ByteCodeExprGen.cpp
--- a/clang/lib/AST/Interp/ByteCodeExprGen.cpp
+++ b/clang/lib/AST/Interp/ByteCodeExprGen.cpp
@@ -1022,6 +1022,11 @@
           return DiscardResult ? this->emitPop(T, E) : true;
         });
   case UO_Not:    // ~x
+    if (!this->Visit(SubExpr))
+      return false;
+    if (Optional<PrimType> T = classify(E->getType()))
+      return this->emitComp(*T, E);
+    return false;
   case UO_Real:   // __real x
   case UO_Imag:   // __imag x
   case UO_Extension:
diff --git a/clang/lib/AST/Interp/Integral.h b/clang/lib/AST/Interp/Integral.h
--- a/clang/lib/AST/Interp/Integral.h
+++ b/clang/lib/AST/Interp/Integral.h
@@ -212,6 +212,11 @@
     return false;
   }
 
+  static bool comp(Integral A, Integral *R) {
+    *R = Integral(~A.V);
+    return false;
+  }
+
 private:
   template <typename T> static bool CheckAddUB(T A, T B, T &R) {
     if constexpr (std::is_signed_v<T>) {
diff --git a/clang/lib/AST/Interp/Interp.h b/clang/lib/AST/Interp/Interp.h
--- a/clang/lib/AST/Interp/Interp.h
+++ b/clang/lib/AST/Interp/Interp.h
@@ -183,6 +183,20 @@
   return true;
 }
 
+/// 1) Pops the value from the stack.
+/// 2) Pushes the bitwise complemented value on the stack (~V).
+template <PrimType Name, class T = typename PrimConv<Name>::T>
+bool Comp(InterpState &S, CodePtr OpPC) {
+  const T &Val = S.Stk.pop<T>();
+  T Result;
+  if (!T::comp(Val, &Result)) {
+    S.Stk.push<T>(Result);
+    return true;
+  }
+
+  return false;
+}
+
 //===----------------------------------------------------------------------===//
 // EQ, NE, GT, GE, LT, LE
 //===----------------------------------------------------------------------===//
diff --git a/clang/lib/AST/Interp/Opcodes.td b/clang/lib/AST/Interp/Opcodes.td
--- a/clang/lib/AST/Interp/Opcodes.td
+++ b/clang/lib/AST/Interp/Opcodes.td
@@ -411,6 +411,12 @@
   let HasGroup = 1;
 }
 
+// [Real] -> [Real]
+def Comp: Opcode {
+  let Types = [NumberTypeClass];
+  let HasGroup = 1;
+}
+
 //===----------------------------------------------------------------------===//
 // Cast.
 //===----------------------------------------------------------------------===//
diff --git a/clang/test/AST/Interp/literals.cpp b/clang/test/AST/Interp/literals.cpp
--- a/clang/test/AST/Interp/literals.cpp
+++ b/clang/test/AST/Interp/literals.cpp
@@ -3,6 +3,10 @@
 // RUN: %clang_cc1 -std=c++11 -verify=ref %s
 // RUN: %clang_cc1 -std=c++20 -verify=ref %s
 
+#define INT_MIN (~__INT_MAX__)
+#define INT_MAX __INT_MAX__
+
+
 static_assert(true, "");
 static_assert(false, ""); // expected-error{{failed}} ref-error{{failed}}
 static_assert(nullptr == nullptr, "");
@@ -66,6 +70,18 @@
 static_assert(-true, "");
 static_assert(-false, ""); //expected-error{{failed}} ref-error{{failed}}
 
+static_assert(~0 == -1, "");
+static_assert(~1 == -2, "");
+static_assert(~-1 == 0, "");
+static_assert(~255 == -256, "");
+static_assert(~INT_MIN == INT_MAX, "");
+static_assert(~INT_MAX == INT_MIN, "");
+
+enum E {};
+constexpr E e = static_cast<E>(0);
+static_assert(~e == -1, "");
+
+
 constexpr int m = 10;
 constexpr const int *p = &m;
 static_assert(p != nullptr, "");