diff --git a/cpython-unix/build-cpython.sh b/cpython-unix/build-cpython.sh
index e3188aa2..d21533a8 100755
--- a/cpython-unix/build-cpython.sh
+++ b/cpython-unix/build-cpython.sh
@@ -365,6 +365,16 @@ if [[ -n "${PYTHON_MEETS_MINIMUM_VERSION_3_12}" && "${TARGET_TRIPLE}" = "ppc64le
     LDFLAGS="${LDFLAGS} -Wl,--no-tls-get-addr-optimize"
 fi
 
+# We're calling install_name_tool -add_rpath on extension modules, which
+# eats up 0x20 bytes of space in the Mach-O header, and we need to make
+# sure there's still enough room to add a code signature (0x10 bytes) on
+# non-arm64 where there's no automatic ad-hoc signature. We are somehow
+# on a toolchain that doesn't make sure there's enough space by default
+# so give it plenty of space.
+if [[ "${PYBUILD_PLATFORM}" = macos* ]]; then
+    LDFLAGS="${LDFLAGS} -Wl,-headerpad,40"
+fi
+
 CPPFLAGS=$CFLAGS
 
 CONFIGURE_FLAGS="
diff --git a/src/validation.rs b/src/validation.rs
index 2fd47867..33e61e2e 100644
--- a/src/validation.rs
+++ b/src/validation.rs
@@ -12,10 +12,10 @@ use {
             FileHeader32, FileHeader64, ET_DYN, ET_EXEC, SHN_UNDEF, STB_GLOBAL, STB_WEAK, STV_DEFAULT,
             STV_HIDDEN,
         },
-        macho::{MachHeader32, MachHeader64, MH_OBJECT, MH_TWOLEVEL},
+        macho::{LC_CODE_SIGNATURE, MH_OBJECT, MH_TWOLEVEL, MachHeader32, MachHeader64},
         read::{
             elf::{Dyn, FileHeader, SectionHeader, Sym},
-            macho::{LoadCommandVariant, MachHeader, Nlist},
+            macho::{LoadCommandVariant, MachHeader, Nlist, Section, Segment},
             pe::{ImageNtHeaders, PeFile, PeFile32, PeFile64},
         },
         Architecture, Endianness, FileKind, Object, SectionIndex, SymbolScope,
@@ -1264,6 +1264,8 @@ fn validate_macho<Mach: MachHeader<Endian = Endianness>>(
     let mut undefined_symbols = vec![];
     let mut target_version = None;
     let mut sdk_version = None;
+    let mut has_code_signature = false;
+    let mut lowest_file_offset = u64::MAX;
 
     while let Some(load_command) = load_commands.next()? {
         match load_command.variant()? {
@@ -1386,10 +1388,38 @@ fn validate_macho<Mach: MachHeader<Endian = Endianness>>(
                     }
                 }
             }
+            LoadCommandVariant::Segment32(segment, segment_data) => {
+                for section in segment.sections(endian, segment_data)? {
+                    if let Some((offset, _)) = section.file_range(endian) {
+                        lowest_file_offset = lowest_file_offset.min(offset);
+                    }
+                }
+            }
+            LoadCommandVariant::Segment64(segment, segment_data) => {
+                for section in segment.sections(endian, segment_data)? {
+                    if let Some((offset, _)) = section.file_range(endian) {
+                        lowest_file_offset = lowest_file_offset.min(offset);
+                    }
+                }
+            }
+            LoadCommandVariant::LinkeditData(c) if c.cmd.get(endian) == LC_CODE_SIGNATURE => {
+                has_code_signature = true;
+            }
             _ => {}
         }
     }
 
+    let end_of_load_commands =
+        std::mem::size_of_val(header) as u64 + header.sizeofcmds(endian) as u64;
+    if header.filetype(endian) != MH_OBJECT
+        && end_of_load_commands + if has_code_signature { 0 } else { 16 } > lowest_file_offset
+    {
+        context.errors.push(format!(
+            "{}: Insufficient headerpad between end of load commands {end_of_load_commands:#x} and beginning of code {lowest_file_offset:#x}",
+            path.display(),
+        ));
+    }
+
     if let Some(actual_target_version) = target_version {
         if actual_target_version != advertised_target_version {
             context.errors.push(format!(