diff --git a/.github/workflows/windows-ci.yml b/.github/workflows/windows-ci.yml
index efa3fc1f92..8f61df5d67 100644
--- a/.github/workflows/windows-ci.yml
+++ b/.github/workflows/windows-ci.yml
@@ -145,6 +145,7 @@ jobs:
           ccache --set-config=max_size=32M
           ccache --set-config=compression=true
           ccache -p
+          export HB_WITH_OPENSSL="/usr/include"
           EOCCACHE
               ;;
           esac
diff --git a/ChangeLog.txt b/ChangeLog.txt
index 2f8dcbcf60..f77e4f0ea8 100644
--- a/ChangeLog.txt
+++ b/ChangeLog.txt
@@ -7,6 +7,18 @@
    Entries may not always be in chronological/commit order.
    See license at the end of file. */
 
+2025-10-20 10:47 UTC+0200 Aleksander Czajczynski (hb fki.pl)
+  * .github/workflows/windows-ci.yml
+    * encourage to test OpenSSL
+
+  * contrib/hbssl/hbssl.hbc
+    * treat Microsoft Visual Studio 2017 or newer can use
+      the latest OpenSSL lib. That's very loose approximation,
+      but hopefully better than before. If you are using such
+      compiler please update your OpenSSL library.
+
+    % deduplicated the rules, leftovers from old static "_s" suffixing
+
 2025-10-19 22:48 UTC+0200 Aleksander Czajczynski (hb fki.pl)
   * .github/workflows/windows-ci.yml
     + add openssl-devel to MSYS2 CI
diff --git a/contrib/hbssl/hbssl.hbc b/contrib/hbssl/hbssl.hbc
index 01441c466f..fdf15ad407 100644
--- a/contrib/hbssl/hbssl.hbc
+++ b/contrib/hbssl/hbssl.hbc
@@ -13,10 +13,8 @@ skip={dos}
 
 {!HB_DYNBIND_OPENSSL&unix}libs=ssl crypto
 {!HB_DYNBIND_OPENSSL&os2}libs=libssl_s libcrypto_s
-{!HB_DYNBIND_OPENSSL&!(HB_STATIC_OPENSSL&!hbdyn)&win&!allmingw&!clang&!zig}libs=ssleay32 libeay32
-{!HB_DYNBIND_OPENSSL& (HB_STATIC_OPENSSL&!hbdyn)&win&!allmingw&!clang&!zig}libs=ssleay32 libeay32
-{!HB_DYNBIND_OPENSSL&!(HB_STATIC_OPENSSL&!hbdyn)&win&(clang|zig)}libs=ssl crypto
-{!HB_DYNBIND_OPENSSL& (HB_STATIC_OPENSSL&!hbdyn)&win&(clang|zig)}libs=ssl crypto
-{!HB_DYNBIND_OPENSSL&!(HB_STATIC_OPENSSL&!hbdyn)&allmingw}libs=ssl crypto
-{!HB_DYNBIND_OPENSSL& (HB_STATIC_OPENSSL&!hbdyn)&allmingw}libs=ssl crypto
-{!HB_DYNBIND_OPENSSL& (HB_STATIC_OPENSSL&!hbdyn)&allwin}libs=crypt32
+{!HB_DYNBIND_OPENSSL&win&!allmingw&!allmsvc&!clang&!zig}libs=ssleay32 libeay32
+{!HB_DYNBIND_OPENSSL&allmsvc&HB_COMP_VER<'1401'}libs=ssleay32 libeay32
+{!HB_DYNBIND_OPENSSL&win&(allmingw|clang|zig)}libs=ssl crypto
+{!HB_DYNBIND_OPENSSL&allmsvc&HB_COMP_VER>'1400'}libs=ssl crypto
+{!HB_DYNBIND_OPENSSL&allwin}libs=crypt32