diff --git a/Include/internal/pycore_stackref.h b/Include/internal/pycore_stackref.h
index 94fcb1d8aee52b..15a703a08204da 100644
--- a/Include/internal/pycore_stackref.h
+++ b/Include/internal/pycore_stackref.h
@@ -403,7 +403,8 @@ PyStackRef_IsTaggedInt(_PyStackRef i)
 static inline _PyStackRef
 PyStackRef_TagInt(intptr_t i)
 {
-    assert(Py_ARITHMETIC_RIGHT_SHIFT(intptr_t, (i << Py_TAGGED_SHIFT), Py_TAGGED_SHIFT) == i);
+    assert(Py_ARITHMETIC_RIGHT_SHIFT(intptr_t, (intptr_t)(((uintptr_t)i) << Py_TAGGED_SHIFT),
+                                     Py_TAGGED_SHIFT) == i);
     return (_PyStackRef){ .bits = ((((uintptr_t)i) << Py_TAGGED_SHIFT) | Py_INT_TAG) };
 }
 
diff --git a/Misc/NEWS.d/next/Build/2025-10-25-08-07-06.gh-issue-140513.6OhLTs.rst b/Misc/NEWS.d/next/Build/2025-10-25-08-07-06.gh-issue-140513.6OhLTs.rst
new file mode 100644
index 00000000000000..1035ebf8d781cf
--- /dev/null
+++ b/Misc/NEWS.d/next/Build/2025-10-25-08-07-06.gh-issue-140513.6OhLTs.rst
@@ -0,0 +1,2 @@
+Generate a clear compilation error when ``_Py_TAIL_CALL_INTERP`` is enabled but
+either ``preserve_none`` or ``musttail`` is not supported.
diff --git a/Python/ceval_macros.h b/Python/ceval_macros.h
index 8083913b1a1cfc..868ab6f755874f 100644
--- a/Python/ceval_macros.h
+++ b/Python/ceval_macros.h
@@ -79,6 +79,14 @@
 #endif
 
 #if _Py_TAIL_CALL_INTERP
+#   if defined(__clang__) || defined(__GNUC__)
+#       if !_Py__has_attribute(preserve_none) || !_Py__has_attribute(musttail)
+#           error "This compiler does not have support for efficient tail calling."
+#       endif
+#   elif defined(_MSC_VER) && (_MSC_VER < 1950)
+#       error "You need at least VS 2026 / PlatformToolset v145 for tail calling."
+#   endif
+
     // Note: [[clang::musttail]] works for GCC 15, but not __attribute__((musttail)) at the moment.
 #   define Py_MUSTTAIL [[clang::musttail]]
 #   define Py_PRESERVE_NONE_CC __attribute__((preserve_none))
diff --git a/Tools/jit/template.c b/Tools/jit/template.c
index 8f71010a1aff58..2f146014a1c26b 100644
--- a/Tools/jit/template.c
+++ b/Tools/jit/template.c
@@ -69,9 +69,11 @@ do {                                                \
     } while (0)
 
 #undef LLTRACE_RESUME_FRAME
-#define LLTRACE_RESUME_FRAME() \
-    do {                       \
-    } while (0)
+#ifdef Py_DEBUG
+#define LLTRACE_RESUME_FRAME() (frame->lltrace = 0)
+#else
+#define LLTRACE_RESUME_FRAME() do {} while (0)
+#endif
 
 #define PATCH_JUMP(ALIAS)                                                 \
 do {                                                                      \