diff --git a/ChangeLog.txt b/ChangeLog.txt
index b619382e2f..96445c4498 100644
--- a/ChangeLog.txt
+++ b/ChangeLog.txt
@@ -7,6 +7,33 @@
    Entries may not always be in chronological/commit order.
    See license at the end of file. */
 
+2025-10-19 22:12 UTC+0200 Aleksander Czajczynski (hb fki.pl)
+  * contrib/hbssl/hbssl.h
+  * contrib/hbssl/hbssl.hbm
+  * contrib/hbssl/ssl.c
+    ! HB_OPENSSL_HAS_APPLINK was never checked,
+      defining HB_OPENSSL_NO_APPLINK didn't do anything
+
+    * make current OpenSSL 3.6.0 build under fresh MSYS2
+      shell. MSYS2 does not distribute applink.c, claiming
+      MingGW C runtime is safe for operation without it.
+      Have to define HB_OPENSSL_NO_APPLINK and additional
+      workaround for lacking __int64 type when including
+      ssl.h. If you need similar workround outside of
+      MSYS2 shell, setenv: HB_USER_CFLAGS=-DHB_OPENSSL_MSYS
+
+      packages needed: openssl-devel (for headers)
+                       mingw-w64-x86_64-openssl (for libs)
+                       mingw-w64-aarch64-openssl
+
+  * contrib/hbssl/hbssl.hbc
+    * using Clang or Zig compiler on Windows, build will
+      now reference libssl and libcrypto instead of old
+      ssleay32/libeay32 pair when linking.
+
+  * config/win/zig.mk
+    % unnecessary check
+
 2025-10-18 23:15 UTC+0200 Aleksander Czajczynski (hb fki.pl)
   + config/bsd/zig-noauto.mk
   + config/bsd/zig.mk
diff --git a/config/win/zig.mk b/config/win/zig.mk
index 3d2ec49c8c..53a806ad69 100644
--- a/config/win/zig.mk
+++ b/config/win/zig.mk
@@ -3,8 +3,6 @@ RCFLAGS := /I. /I$(HB_HOST_INC) /C 1252
 RC_OUT := /FO$(subst x,x, )
 RES_EXT := .res
 
-ifeq ($(HB_PLATFORM),win)
-   IMPLIBFLAGS = -Wl,--out-implib,$(IMP_FILE)
-endif
+IMPLIBFLAGS = -Wl,--out-implib,$(IMP_FILE)
 
 include $(TOP)$(ROOT)config/common/zig.mk
diff --git a/contrib/hbssl/hbssl.h b/contrib/hbssl/hbssl.h
index 9ce82b327f..835a8686fc 100644
--- a/contrib/hbssl/hbssl.h
+++ b/contrib/hbssl/hbssl.h
@@ -62,6 +62,18 @@
    #endif
 #endif
 
+/* following can be defined if MSYS/MinGW64 toolchain complains about lacking
+    '__int64' type inside OpenSSL project headers, also applink.c is not
+     needed on MinGW C runtime - therefore applink.c is not distributed there */
+#if defined( HB_OPENSSL_MSYS )
+   #ifdef __MINGW64__
+      #include <basetsd.h>
+   #endif
+   #if ! defined( HB_OPENSSL_NO_APPLINK )
+      #define HB_OPENSSL_NO_APPLINK
+   #endif
+#endif
+
 #include <openssl/ssl.h>
 
 #include "hbssl.ch"
diff --git a/contrib/hbssl/hbssl.hbc b/contrib/hbssl/hbssl.hbc
index 0a77ba5f97..01441c466f 100644
--- a/contrib/hbssl/hbssl.hbc
+++ b/contrib/hbssl/hbssl.hbc
@@ -13,8 +13,10 @@ 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}libs=ssleay32 libeay32
-{!HB_DYNBIND_OPENSSL& (HB_STATIC_OPENSSL&!hbdyn)&win&!allmingw}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&!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
diff --git a/contrib/hbssl/hbssl.hbm b/contrib/hbssl/hbssl.hbm
index d88f5c31e4..0de61913b3 100644
--- a/contrib/hbssl/hbssl.hbm
+++ b/contrib/hbssl/hbssl.hbm
@@ -31,6 +31,9 @@
 # Patent expires in 2010/2011
 -cflag=-DOPENSSL_NO_IDEA
 
+# MSYS2 lacks applink.c and __int64
+{MSYSTEM}-cflag=-DHB_OPENSSL_MSYS
+
 # to suppress Apple's deprecation warnings that apply to
 # the complete OpenSSL API, starting with OS X Lion 10.7
 -cflag={allgcc&darwin}-Wno-deprecated
diff --git a/contrib/hbssl/ssl.c b/contrib/hbssl/ssl.c
index 6fca5b76ba..6f43fe73f9 100644
--- a/contrib/hbssl/ssl.c
+++ b/contrib/hbssl/ssl.c
@@ -82,6 +82,7 @@
 #if ! defined( HB_OPENSSL_NO_APPLINK ) && \
     defined( HB_OS_WIN ) && \
     defined( HB_CPU_X86 ) && \
+    ! defined( HB_OPENSSL_STATIC ) && \
     OPENSSL_VERSION_NUMBER >= 0x00908000L
    /* Enable this to add support for various scenarios when
       OpenSSL is build with OPENSSL_USE_APPLINK (the default).
@@ -93,7 +94,7 @@
 /* NOTE: See: http://www.openssl.org/support/faq.html#PROG2
          Application must call SSL_init(), so that this module gets linked.
          [vszakats] */
-#if defined( HB_OS_WIN ) && ! defined( HB_OPENSSL_STATIC ) && OPENSSL_VERSION_NUMBER >= 0x00908000L
+#if defined( HB_OPENSSL_HAS_APPLINK )
    /* Pull a stub that returns a table with some selected
       C RTL function pointers. When linking to OpenSSL shared
       libraries, the function OPENSSL_Applink() exported from