diff --git a/Misc/NEWS.d/next/macOS/2023-12-23-22-41-07.gh-issue-110459.NaMBJy.rst b/Misc/NEWS.d/next/macOS/2023-12-23-22-41-07.gh-issue-110459.NaMBJy.rst
new file mode 100644
index 00000000000000..44ffd857785f0d
--- /dev/null
+++ b/Misc/NEWS.d/next/macOS/2023-12-23-22-41-07.gh-issue-110459.NaMBJy.rst
@@ -0,0 +1,2 @@
+Running ``configure ... --with-openssl-rpath=X/Y/Z`` no longer fails to detect
+OpenSSL on macOS.
diff --git a/configure b/configure
index 99dd1fe595805e..89cb0af392e556 100755
--- a/configure
+++ b/configure
@@ -28114,7 +28114,12 @@ then :
 
 else $as_nop
 
-  rpath_arg="-Wl,-rpath="
+  if test "$ac_sys_system" = "Darwin"
+  then
+     rpath_arg="-Wl,-rpath,"
+  else
+     rpath_arg="-Wl,-rpath="
+  fi
 
 fi
 
diff --git a/configure.ac b/configure.ac
index bd2be94b47cb9c..4ae70a10ef8141 100644
--- a/configure.ac
+++ b/configure.ac
@@ -7002,7 +7002,12 @@ AX_CHECK_OPENSSL([have_openssl=yes],[have_openssl=no])
 AS_VAR_IF([GNULD], [yes], [
   rpath_arg="-Wl,--enable-new-dtags,-rpath="
 ], [
-  rpath_arg="-Wl,-rpath="
+  if test "$ac_sys_system" = "Darwin"
+  then
+     rpath_arg="-Wl,-rpath,"
+  else
+     rpath_arg="-Wl,-rpath="
+  fi
 ])
 
 AC_MSG_CHECKING([for --with-openssl-rpath])