diff --git a/Kernel/Memory/Region.h b/Kernel/Memory/Region.h
index 3383d1aaa96..f2807a4cbe6 100644
--- a/Kernel/Memory/Region.h
+++ b/Kernel/Memory/Region.h
@@ -102,6 +102,9 @@ public:
         m_mmapped_from_writable = description_was_writable;
     }
 
+    [[nodiscard]] bool is_initially_loaded_executable_segment() const { return m_initially_loaded_executable_segment.was_set(); }
+    void set_initially_loaded_executable_segment() { m_initially_loaded_executable_segment.set(); }
+
     [[nodiscard]] bool is_write_combine() const { return m_write_combine; }
     ErrorOr<void> set_write_combine(bool);
 
@@ -250,6 +253,7 @@ private:
     bool m_mmapped_from_writable : 1 { false };
 
     SetOnce m_immutable;
+    SetOnce m_initially_loaded_executable_segment;
 
     IntrusiveRedBlackTreeNode<FlatPtr, Region, RawPtr<Region>> m_tree_node;
     IntrusiveListNode<Region> m_vmobject_list_node;
diff --git a/Kernel/Syscalls/execve.cpp b/Kernel/Syscalls/execve.cpp
index 0e9cdccfb02..140a49337d6 100644
--- a/Kernel/Syscalls/execve.cpp
+++ b/Kernel/Syscalls/execve.cpp
@@ -347,6 +347,8 @@ static ErrorOr<LoadResult> load_elf_object(Memory::AddressSpace& new_space, Open
         size_t rounded_range_end = TRY(Memory::page_round_up(program_header.vaddr().offset(load_offset).offset(program_header.size_in_memory()).get()));
         auto range_end = VirtualAddress { rounded_range_end };
         auto region = TRY(new_space.allocate_region_with_vmobject(Memory::RandomizeVirtualAddress::Yes, range_base, range_end.get() - range_base.get(), program_header.alignment(), *vmobject, program_header.offset(), elf_name->view(), prot, true));
+        if (program_header.is_executable())
+            region->set_initially_loaded_executable_segment();
 
         if (should_allow_syscalls == ShouldAllowSyscalls::Yes)
             region->set_syscall_region(true);
diff --git a/Kernel/Syscalls/mmap.cpp b/Kernel/Syscalls/mmap.cpp
index 72a849f165e..eb07ad386d8 100644
--- a/Kernel/Syscalls/mmap.cpp
+++ b/Kernel/Syscalls/mmap.cpp
@@ -542,7 +542,7 @@ ErrorOr<FlatPtr> Process::sys$annotate_mapping(Userspace<void*> address, int fla
         if (!region)
             return EINVAL;
 
-        if (!region->is_mmap())
+        if (!region->is_mmap() && !region->is_initially_loaded_executable_segment())
             return EINVAL;
         if (region->is_immutable())
             return EPERM;