diff --git a/Misc/NEWS.d/next/Build/2026-09-18-15-00-00.gh-issue-157755.ssl-order.rst b/Misc/NEWS.d/next/Build/2026-09-18-15-00-00.gh-issue-157755.ssl-order.rst
new file mode 100644
index 000000000000000..5810deaf7c058e7
--- /dev/null
+++ b/Misc/NEWS.d/next/Build/2026-09-18-15-00-00.gh-issue-157755.ssl-order.rst
@@ -0,0 +1,3 @@
+Fix OpenSSL API checks in configure when static OpenSSL libraries depend on
+libraries supplied through ``LIBS``. Place the OpenSSL libraries before their
+dependencies in the link command.
diff --git a/configure b/configure
index 1115be256afb495..c21ccc52513f897 100755
--- a/configure
+++ b/configure
@@ -34877,7 +34877,7 @@ save_LDFLAGS=$LDFLAGS
 save_LIBS=$LIBS
 
 
-  LIBS="$LIBS $OPENSSL_LIBS"
+  LIBS="$OPENSSL_LIBS $LIBS"
   CFLAGS="$CFLAGS $OPENSSL_INCLUDES"
   LDFLAGS="$LDFLAGS $OPENSSL_LDFLAGS $OPENSSL_LDFLAGS_RPATH"
 
@@ -34942,7 +34942,7 @@ save_LDFLAGS=$LDFLAGS
 save_LIBS=$LIBS
 
 
-  LIBS="$LIBS $LIBCRYPTO_LIBS"
+  LIBS="$LIBCRYPTO_LIBS $LIBS"
   CFLAGS="$CFLAGS $OPENSSL_INCLUDES"
   LDFLAGS="$LDFLAGS $OPENSSL_LDFLAGS $OPENSSL_LDFLAGS_RPATH"
 
diff --git a/configure.ac b/configure.ac
index 902a822e43a42f0..96be23149b05325 100644
--- a/configure.ac
+++ b/configure.ac
@@ -8045,7 +8045,7 @@ done
 
 # check if OpenSSL libraries work as expected
 WITH_SAVE_ENV([
-  LIBS="$LIBS $OPENSSL_LIBS"
+  LIBS="$OPENSSL_LIBS $LIBS"
   CFLAGS="$CFLAGS $OPENSSL_INCLUDES"
   LDFLAGS="$LDFLAGS $OPENSSL_LDFLAGS $OPENSSL_LDFLAGS_RPATH"
 
@@ -8070,7 +8070,7 @@ WITH_SAVE_ENV([
 ])
 
 WITH_SAVE_ENV([
-  LIBS="$LIBS $LIBCRYPTO_LIBS"
+  LIBS="$LIBCRYPTO_LIBS $LIBS"
   CFLAGS="$CFLAGS $OPENSSL_INCLUDES"
   LDFLAGS="$LDFLAGS $OPENSSL_LDFLAGS $OPENSSL_LDFLAGS_RPATH"