diff --git a/src/PackageCompiler.jl b/src/PackageCompiler.jl
index 631536c5..343e18dc 100644
--- a/src/PackageCompiler.jl
+++ b/src/PackageCompiler.jl
@@ -711,7 +711,23 @@ function create_sysimg_from_object_file(object_files::Vector{String},
     end
     mkpath(dirname(sysimage_path))
     # Prevent compiler from stripping all symbols from the shared lib.
-    o_file_flags = Sys.isapple() ? `-Wl,-all_load $object_files` : `-Wl,--whole-archive $object_files -Wl,--no-whole-archive`
+    if Sys.isapple()
+        try
+            cltools_version_cmd = `pkgutil --pkg-info=com.apple.pkg.CLTools_Executables`
+            cltools_version = match(r"version: (.*)\n", readchomp(cltools_version_cmd))[1]
+            global major_version = split(cltools_version, ".")[1]
+        catch e
+            @warn "Could not determine the version of the Command Line Tools, assuming greater than 14"
+            global major_version = "15"
+        end
+        if parse(Int64, major_version) > 14
+            o_file_flags = `-Wl,-all_load $object_files -Wl,-ld_classic`
+        else
+            o_file_flags = `-Wl,-all_load $object_files`
+        end
+    else
+        o_file_flags = `-Wl,--whole-archive $object_files -Wl,--no-whole-archive`
+    end
     extra = get_extra_linker_flags(version, compat_level, soname)
     cmd = `$(bitflag()) $(march()) -shared -L$(julia_libdir()) -L$(julia_private_libdir()) -o $sysimage_path $o_file_flags $(Base.shell_split(ldlibs())) $extra`
     run_compiler(cmd; cplusplus=true)