diff --git a/contrib/win32/openssh/config.h.vs b/contrib/win32/openssh/config.h.vs
index 721f62ba9..16e2458be 100644
--- a/contrib/win32/openssh/config.h.vs
+++ b/contrib/win32/openssh/config.h.vs
@@ -1736,5 +1736,37 @@
 #define HAVE_STRUCT_POLLFD_FD 1
 #define HAVE_KILLPG 1
 
+/* Definitions needed to prevent re-definition of OpenSSL functions and structs */
+#define HAVE_DSA_GET0_PQG 1
+#define HAVE_DSA_SET0_PQG 1
+#define HAVE_DSA_GET0_KEY 1
+#define HAVE_DSA_SET0_KEY 1
+#define HAVE_RSA_GET0_KEY 1
+#define HAVE_RSA_SET0_KEY 1
+#define HAVE_RSA_GET0_CRT_PARAMS 1
+#define HAVE_RSA_SET0_CRT_PARAMS 1
+#define HAVE_RSA_GET0_FACTORS 1
+#define HAVE_RSA_SET0_FACTORS 1
+#define HAVE_EVP_CIPHER_CTX_GET_IV 1
+#define HAVE_EVP_CIPHER_CTX_SET_IV 1
+#define HAVE_DSA_SIG_GET0 1
+#define HAVE_DSA_SIG_SET0 1
+#define HAVE_ECDSA_SIG_GET0 1
+#define HAVE_ECDSA_SIG_SET0 1
+#define HAVE_DH_GET0_PQG 1
+#define HAVE_DH_SET0_PQG 1
+#define HAVE_DH_GET0_KEY 1
+#define HAVE_DH_SET0_KEY 1
+#define HAVE_DH_SET_LENGTH 1
+#define HAVE_RSA_METH_FREE 1
+#define HAVE_RSA_METH_DUP 1
+#define HAVE_RSA_METH_SET1_NAME 1
+#define HAVE_RSA_METH_GET_FINISH 1
+#define HAVE_RSA_METH_SET_PRIV_ENC 1
+#define HAVE_RSA_METH_SET_PRIV_DEC 1
+#define HAVE_RSA_METH_SET_FINISH 1
+#define HAVE_EVP_PKEY_GET0_RSA 1
+#define HAVE_EVP_MD_CTX_NEW 1
+#define HAVE_EVP_MD_CTX_FREE 1
 
 
diff --git a/contrib/win32/openssh/paths.targets b/contrib/win32/openssh/paths.targets
index 84dfa65bb..5232c5dd8 100644
--- a/contrib/win32/openssh/paths.targets
+++ b/contrib/win32/openssh/paths.targets
@@ -4,9 +4,9 @@
     <OpenSSH-Src-Path>$(SolutionDir)..\..\..\</OpenSSH-Src-Path>
     <OpenSSH-Bin-Path>$(SolutionDir)..\..\..\bin\</OpenSSH-Bin-Path>
     <OpenSSH-Lib-Path>$(SolutionDir)lib\</OpenSSH-Lib-Path>
-    <LibreSSLVersion>3.4.3.0</LibreSSLVersion>
-    <ZLibVersion>1.2.11</ZLibVersion>
-    <fido2Version>1.10.0</fido2Version>
+    <LibreSSLVersion>3.6.1.0</LibreSSLVersion>
+    <ZLibVersion>1.2.13</ZLibVersion>
+    <fido2Version>1.12.0</fido2Version>
     <!--libcbor version is not used in the bulid; it is needed for pipeline compliance tasks-->  
     <libcborVersion>0.8.0</libcborVersion> 
     <LibreSSL-Path>$(SolutionDir)\LibreSSL\sdk\</LibreSSL-Path>
diff --git a/contrib/win32/openssh/unittest-bitmap.vcxproj b/contrib/win32/openssh/unittest-bitmap.vcxproj
index 0d86c3cc9..b2ed3a8d6 100644
--- a/contrib/win32/openssh/unittest-bitmap.vcxproj
+++ b/contrib/win32/openssh/unittest-bitmap.vcxproj
@@ -201,6 +201,9 @@
       <AdditionalDependencies>posix_compat.lib;libssh.lib;openbsd_compat.lib;$(SSLLib)$(AdditionalDependentLibs);%(AdditionalDependencies)</AdditionalDependencies>
       <EntryPointSymbol>wmainCRTStartup</EntryPointSymbol>
     </Link>
+    <PostBuildEvent>
+      <command>copy /Y "$(LibreSSL-x86-Path)\libcrypto.dll" "$(OutDir)"</command>
+    </PostBuildEvent>
     <Manifest>
       <AdditionalManifestFiles>targetos.manifest</AdditionalManifestFiles>
     </Manifest>
@@ -224,6 +227,9 @@
       <AdditionalDependencies>posix_compat.lib;libssh.lib;openbsd_compat.lib;$(SSLLib)$(AdditionalDependentLibs);%(AdditionalDependencies)</AdditionalDependencies>
       <EntryPointSymbol>wmainCRTStartup</EntryPointSymbol>
     </Link>
+    <PostBuildEvent>
+      <command>copy /Y "$(LibreSSL-x64-Path)\libcrypto.dll" "$(OutDir)"</command>
+    </PostBuildEvent>
     <Manifest>
       <AdditionalManifestFiles>targetos.manifest</AdditionalManifestFiles>
     </Manifest>
@@ -247,6 +253,9 @@
       <AdditionalDependencies>posix_compat.lib;libssh.lib;openbsd_compat.lib;$(SSLLib)$(AdditionalDependentLibs);%(AdditionalDependencies)</AdditionalDependencies>
       <EntryPointSymbol>wmainCRTStartup</EntryPointSymbol>
     </Link>
+    <PostBuildEvent>
+      <command>copy /Y "$(LibreSSL-arm64-Path)\libcrypto.dll" "$(OutDir)"</command>
+    </PostBuildEvent>
     <Manifest>
       <AdditionalManifestFiles>targetos.manifest</AdditionalManifestFiles>
     </Manifest>
@@ -270,6 +279,9 @@
       <AdditionalDependencies>posix_compat.lib;libssh.lib;openbsd_compat.lib;$(SSLLib)$(AdditionalDependentLibs);%(AdditionalDependencies)</AdditionalDependencies>
       <EntryPointSymbol>wmainCRTStartup</EntryPointSymbol>
     </Link>
+    <PostBuildEvent>
+      <command>copy /Y "$(LibreSSL-arm-Path)\libcrypto.dll" "$(OutDir)"</command>
+    </PostBuildEvent>
     <Manifest>
       <AdditionalManifestFiles>targetos.manifest</AdditionalManifestFiles>
     </Manifest>
@@ -295,6 +307,9 @@
       <AdditionalDependencies>posix_compat.lib;libssh.lib;openbsd_compat.lib;$(SSLLib)$(AdditionalDependentLibs);%(AdditionalDependencies)</AdditionalDependencies>
       <EntryPointSymbol>wmainCRTStartup</EntryPointSymbol>
     </Link>
+    <PostBuildEvent>
+      <command>copy /Y "$(LibreSSL-x86-Path)\libcrypto.dll" "$(OutDir)"</command>
+    </PostBuildEvent>
     <Manifest>
       <AdditionalManifestFiles>targetos.manifest</AdditionalManifestFiles>
     </Manifest>
@@ -321,6 +336,9 @@
       <AdditionalDependencies>posix_compat.lib;libssh.lib;openbsd_compat.lib;$(SSLLib)$(AdditionalDependentLibs);%(AdditionalDependencies)</AdditionalDependencies>
       <EntryPointSymbol>wmainCRTStartup</EntryPointSymbol>
     </Link>
+    <PostBuildEvent>
+      <command>copy /Y "$(LibreSSL-x64-Path)\libcrypto.dll" "$(OutDir)"</command>
+    </PostBuildEvent>
     <Manifest>
       <AdditionalManifestFiles>targetos.manifest</AdditionalManifestFiles>
     </Manifest>
@@ -347,6 +365,9 @@
       <AdditionalDependencies>posix_compat.lib;libssh.lib;openbsd_compat.lib;$(SSLLib)$(AdditionalDependentLibs);%(AdditionalDependencies)</AdditionalDependencies>
       <EntryPointSymbol>wmainCRTStartup</EntryPointSymbol>
     </Link>
+    <PostBuildEvent>
+      <command>copy /Y "$(LibreSSL-arm64-Path)\libcrypto.dll" "$(OutDir)"</command>
+    </PostBuildEvent>
     <Manifest>
       <AdditionalManifestFiles>targetos.manifest</AdditionalManifestFiles>
     </Manifest>
@@ -373,6 +394,9 @@
       <AdditionalDependencies>posix_compat.lib;libssh.lib;openbsd_compat.lib;$(SSLLib)$(AdditionalDependentLibs);%(AdditionalDependencies)</AdditionalDependencies>
       <EntryPointSymbol>wmainCRTStartup</EntryPointSymbol>
     </Link>
+    <PostBuildEvent>
+      <command>copy /Y "$(LibreSSL-arm-Path)\libcrypto.dll" "$(OutDir)"</command>
+    </PostBuildEvent>
     <Manifest>
       <AdditionalManifestFiles>targetos.manifest</AdditionalManifestFiles>
     </Manifest>
diff --git a/contrib/win32/openssh/unittest-hostkeys.vcxproj b/contrib/win32/openssh/unittest-hostkeys.vcxproj
index a3f210ac6..4fc54a7e9 100644
--- a/contrib/win32/openssh/unittest-hostkeys.vcxproj
+++ b/contrib/win32/openssh/unittest-hostkeys.vcxproj
@@ -205,7 +205,8 @@
       <AdditionalManifestFiles>targetos.manifest</AdditionalManifestFiles>
     </Manifest>
     <PostBuildEvent>
-      <Command>xcopy /Y "$(ProjectDir)..\..\..\regress\unittests\hostkeys\testdata\*" "$(OutDir)"</Command>
+      <Command>xcopy /Y "$(ProjectDir)..\..\..\regress\unittests\hostkeys\testdata\*" "$(OutDir)"
+copy /Y "$(LibreSSL-x86-Path)\libcrypto.dll" "$(OutDir)"</Command>
     </PostBuildEvent>
   </ItemDefinitionGroup>
   <ItemDefinitionGroup Condition="'$(Configuration)|$(Platform)'=='Debug|x64'">
@@ -231,7 +232,8 @@
       <AdditionalManifestFiles>targetos.manifest</AdditionalManifestFiles>
     </Manifest>
     <PostBuildEvent>
-      <Command>xcopy /Y "$(ProjectDir)..\..\..\regress\unittests\hostkeys\testdata\*" "$(OutDir)"</Command>
+      <Command>xcopy /Y "$(ProjectDir)..\..\..\regress\unittests\hostkeys\testdata\*" "$(OutDir)"
+copy /Y "$(LibreSSL-x64-Path)\libcrypto.dll" "$(OutDir)"</Command>
     </PostBuildEvent>
   </ItemDefinitionGroup>
   <ItemDefinitionGroup Condition="'$(Configuration)|$(Platform)'=='Debug|ARM64'">
@@ -257,7 +259,8 @@
       <AdditionalManifestFiles>targetos.manifest</AdditionalManifestFiles>
     </Manifest>
     <PostBuildEvent>
-      <Command>xcopy /Y "$(ProjectDir)..\..\..\regress\unittests\hostkeys\testdata\*" "$(OutDir)"</Command>
+      <Command>xcopy /Y "$(ProjectDir)..\..\..\regress\unittests\hostkeys\testdata\*" "$(OutDir)"
+copy /Y "$(LibreSSL-arm64-Path)\libcrypto.dll" "$(OutDir)"</Command>
     </PostBuildEvent>
   </ItemDefinitionGroup>
   <ItemDefinitionGroup Condition="'$(Configuration)|$(Platform)'=='Debug|ARM'">
@@ -283,7 +286,8 @@
       <AdditionalManifestFiles>targetos.manifest</AdditionalManifestFiles>
     </Manifest>
     <PostBuildEvent>
-      <Command>xcopy /Y "$(ProjectDir)..\..\..\regress\unittests\hostkeys\testdata\*" "$(OutDir)"</Command>
+      <Command>xcopy /Y "$(ProjectDir)..\..\..\regress\unittests\hostkeys\testdata\*" "$(OutDir)"
+copy /Y "$(LibreSSL-arm-Path)\libcrypto.dll" "$(OutDir)"</Command>
     </PostBuildEvent>
   </ItemDefinitionGroup>
   <ItemDefinitionGroup Condition="'$(Configuration)|$(Platform)'=='Release|Win32'">
@@ -311,7 +315,8 @@
       <AdditionalManifestFiles>targetos.manifest</AdditionalManifestFiles>
     </Manifest>
     <PostBuildEvent>
-      <Command>xcopy /Y "$(ProjectDir)..\..\..\regress\unittests\hostkeys\testdata\*" "$(OutDir)"</Command>
+      <Command>xcopy /Y "$(ProjectDir)..\..\..\regress\unittests\hostkeys\testdata\*" "$(OutDir)"
+copy /Y "$(LibreSSL-x86-Path)\libcrypto.dll" "$(OutDir)"</Command>
     </PostBuildEvent>
   </ItemDefinitionGroup>
   <ItemDefinitionGroup Condition="'$(Configuration)|$(Platform)'=='Release|x64'">
@@ -340,7 +345,8 @@
       <AdditionalManifestFiles>targetos.manifest</AdditionalManifestFiles>
     </Manifest>
     <PostBuildEvent>
-      <Command>xcopy /Y "$(ProjectDir)..\..\..\regress\unittests\hostkeys\testdata\*" "$(OutDir)"</Command>
+      <Command>xcopy /Y "$(ProjectDir)..\..\..\regress\unittests\hostkeys\testdata\*" "$(OutDir)"
+copy /Y "$(LibreSSL-x64-Path)\libcrypto.dll" "$(OutDir)"</Command>
     </PostBuildEvent>
   </ItemDefinitionGroup>
   <ItemDefinitionGroup Condition="'$(Configuration)|$(Platform)'=='Release|ARM64'">
@@ -369,7 +375,8 @@
       <AdditionalManifestFiles>targetos.manifest</AdditionalManifestFiles>
     </Manifest>
     <PostBuildEvent>
-      <Command>xcopy /Y "$(ProjectDir)..\..\..\regress\unittests\hostkeys\testdata\*" "$(OutDir)"</Command>
+      <Command>xcopy /Y "$(ProjectDir)..\..\..\regress\unittests\hostkeys\testdata\*" "$(OutDir)"
+copy /Y "$(LibreSSL-arm64-Path)\libcrypto.dll" "$(OutDir)"</Command>
     </PostBuildEvent>
   </ItemDefinitionGroup>
   <ItemDefinitionGroup Condition="'$(Configuration)|$(Platform)'=='Release|ARM'">
@@ -398,7 +405,8 @@
       <AdditionalManifestFiles>targetos.manifest</AdditionalManifestFiles>
     </Manifest>
     <PostBuildEvent>
-      <Command>xcopy /Y "$(ProjectDir)..\..\..\regress\unittests\hostkeys\testdata\*" "$(OutDir)"</Command>
+      <Command>xcopy /Y "$(ProjectDir)..\..\..\regress\unittests\hostkeys\testdata\*" "$(OutDir)"
+copy /Y "$(LibreSSL-arm-Path)\libcrypto.dll" "$(OutDir)"</Command>
     </PostBuildEvent>
   </ItemDefinitionGroup>
   <ItemGroup>
diff --git a/contrib/win32/openssh/unittest-kex.vcxproj b/contrib/win32/openssh/unittest-kex.vcxproj
index e6cf4f777..5e78b5869 100644
--- a/contrib/win32/openssh/unittest-kex.vcxproj
+++ b/contrib/win32/openssh/unittest-kex.vcxproj
@@ -202,6 +202,9 @@
       <EntryPointSymbol>wmainCRTStartup</EntryPointSymbol>
       <AdditionalOptions>/ignore:4099 /ignore:4098 %(AdditionalOptions)</AdditionalOptions>
     </Link>
+    <PostBuildEvent>
+      <command>copy /Y "$(LibreSSL-x86-Path)\libcrypto.dll" "$(OutDir)"</command>
+    </PostBuildEvent>
     <Manifest>
       <AdditionalManifestFiles>targetos.manifest</AdditionalManifestFiles>
     </Manifest>
@@ -226,6 +229,9 @@
       <EntryPointSymbol>wmainCRTStartup</EntryPointSymbol>
       <AdditionalOptions>/ignore:4099 /ignore:4098 %(AdditionalOptions)</AdditionalOptions>
     </Link>
+    <PostBuildEvent>
+      <command>copy /Y "$(LibreSSL-x64-Path)\libcrypto.dll" "$(OutDir)"</command>
+    </PostBuildEvent>
     <Manifest>
       <AdditionalManifestFiles>targetos.manifest</AdditionalManifestFiles>
     </Manifest>
@@ -250,6 +256,9 @@
       <EntryPointSymbol>wmainCRTStartup</EntryPointSymbol>
       <AdditionalOptions>/ignore:4099 /ignore:4098 %(AdditionalOptions)</AdditionalOptions>
     </Link>
+    <PostBuildEvent>
+      <command>copy /Y "$(LibreSSL-arm64-Path)\libcrypto.dll" "$(OutDir)"</command>
+    </PostBuildEvent>
     <Manifest>
       <AdditionalManifestFiles>targetos.manifest</AdditionalManifestFiles>
     </Manifest>
@@ -274,6 +283,9 @@
       <EntryPointSymbol>wmainCRTStartup</EntryPointSymbol>
       <AdditionalOptions>/ignore:4099 /ignore:4098 %(AdditionalOptions)</AdditionalOptions>
     </Link>
+    <PostBuildEvent>
+      <command>copy /Y "$(LibreSSL-arm-Path)\libcrypto.dll" "$(OutDir)"</command>
+    </PostBuildEvent>
     <Manifest>
       <AdditionalManifestFiles>targetos.manifest</AdditionalManifestFiles>
     </Manifest>
@@ -300,6 +312,9 @@
       <EntryPointSymbol>wmainCRTStartup</EntryPointSymbol>
       <AdditionalOptions>/ignore:4099 %(AdditionalOptions)</AdditionalOptions>
     </Link>
+    <PostBuildEvent>
+      <command>copy /Y "$(LibreSSL-x86-Path)\libcrypto.dll" "$(OutDir)"</command>
+    </PostBuildEvent>
     <Manifest>
       <AdditionalManifestFiles>targetos.manifest</AdditionalManifestFiles>
     </Manifest>
@@ -327,6 +342,9 @@
       <EntryPointSymbol>wmainCRTStartup</EntryPointSymbol>
       <AdditionalOptions>/ignore:4099 %(AdditionalOptions)</AdditionalOptions>
     </Link>
+    <PostBuildEvent>
+      <command>copy /Y "$(LibreSSL-x64-Path)\libcrypto.dll" "$(OutDir)"</command>
+    </PostBuildEvent>
     <Manifest>
       <AdditionalManifestFiles>targetos.manifest</AdditionalManifestFiles>
     </Manifest>
@@ -354,6 +372,9 @@
       <EntryPointSymbol>wmainCRTStartup</EntryPointSymbol>
       <AdditionalOptions>/ignore:4099 %(AdditionalOptions)</AdditionalOptions>
     </Link>
+    <PostBuildEvent>
+      <command>copy /Y "$(LibreSSL-arm64-Path)\libcrypto.dll" "$(OutDir)"</command>
+    </PostBuildEvent>
     <Manifest>
       <AdditionalManifestFiles>targetos.manifest</AdditionalManifestFiles>
     </Manifest>
@@ -381,6 +402,9 @@
       <EntryPointSymbol>wmainCRTStartup</EntryPointSymbol>
       <AdditionalOptions>/ignore:4099 %(AdditionalOptions)</AdditionalOptions>
     </Link>
+    <PostBuildEvent>
+      <command>copy /Y "$(LibreSSL-arm-Path)\libcrypto.dll" "$(OutDir)"</command>
+    </PostBuildEvent>
     <Manifest>
       <AdditionalManifestFiles>targetos.manifest</AdditionalManifestFiles>
     </Manifest>
diff --git a/contrib/win32/openssh/unittest-match.vcxproj b/contrib/win32/openssh/unittest-match.vcxproj
index f0ca0e753..41d32c175 100644
--- a/contrib/win32/openssh/unittest-match.vcxproj
+++ b/contrib/win32/openssh/unittest-match.vcxproj
@@ -201,6 +201,9 @@
       <AdditionalDependencies>posix_compat.lib;libssh.lib;openbsd_compat.lib;$(SSLLib)$(AdditionalDependentLibs);%(AdditionalDependencies)</AdditionalDependencies>
       <EntryPointSymbol>wmainCRTStartup</EntryPointSymbol>
     </Link>
+    <PostBuildEvent>
+      <command>copy /Y "$(LibreSSL-x86-Path)\libcrypto.dll" "$(OutDir)"</command>
+    </PostBuildEvent>
     <Manifest>
       <AdditionalManifestFiles>targetos.manifest</AdditionalManifestFiles>
     </Manifest>
@@ -224,6 +227,9 @@
       <AdditionalDependencies>posix_compat.lib;libssh.lib;openbsd_compat.lib;$(SSLLib)$(AdditionalDependentLibs);%(AdditionalDependencies)</AdditionalDependencies>
       <EntryPointSymbol>wmainCRTStartup</EntryPointSymbol>
     </Link>
+    <PostBuildEvent>
+      <command>copy /Y "$(LibreSSL-x64-Path)\libcrypto.dll" "$(OutDir)"</command>
+    </PostBuildEvent>
     <Manifest>
       <AdditionalManifestFiles>targetos.manifest</AdditionalManifestFiles>
     </Manifest>
@@ -247,6 +253,9 @@
       <AdditionalDependencies>posix_compat.lib;libssh.lib;openbsd_compat.lib;$(SSLLib)$(AdditionalDependentLibs);%(AdditionalDependencies)</AdditionalDependencies>
       <EntryPointSymbol>wmainCRTStartup</EntryPointSymbol>
     </Link>
+    <PostBuildEvent>
+      <command>copy /Y "$(LibreSSL-arm64-Path)\libcrypto.dll" "$(OutDir)"</command>
+    </PostBuildEvent>
     <Manifest>
       <AdditionalManifestFiles>targetos.manifest</AdditionalManifestFiles>
     </Manifest>
@@ -270,6 +279,9 @@
       <AdditionalDependencies>posix_compat.lib;libssh.lib;openbsd_compat.lib;$(SSLLib)$(AdditionalDependentLibs);%(AdditionalDependencies)</AdditionalDependencies>
       <EntryPointSymbol>wmainCRTStartup</EntryPointSymbol>
     </Link>
+    <PostBuildEvent>
+      <command>copy /Y "$(LibreSSL-arm-Path)\libcrypto.dll" "$(OutDir)"</command>
+    </PostBuildEvent>
     <Manifest>
       <AdditionalManifestFiles>targetos.manifest</AdditionalManifestFiles>
     </Manifest>
@@ -295,6 +307,9 @@
       <AdditionalDependencies>posix_compat.lib;libssh.lib;openbsd_compat.lib;$(SSLLib)$(AdditionalDependentLibs);%(AdditionalDependencies)</AdditionalDependencies>
       <EntryPointSymbol>wmainCRTStartup</EntryPointSymbol>
     </Link>
+    <PostBuildEvent>
+      <command>copy /Y "$(LibreSSL-x86-Path)\libcrypto.dll" "$(OutDir)"</command>
+    </PostBuildEvent>
     <Manifest>
       <AdditionalManifestFiles>targetos.manifest</AdditionalManifestFiles>
     </Manifest>
@@ -321,6 +336,9 @@
       <AdditionalDependencies>posix_compat.lib;libssh.lib;openbsd_compat.lib;$(SSLLib)$(AdditionalDependentLibs);%(AdditionalDependencies)</AdditionalDependencies>
       <EntryPointSymbol>wmainCRTStartup</EntryPointSymbol>
     </Link>
+    <PostBuildEvent>
+      <command>copy /Y "$(LibreSSL-x64-Path)\libcrypto.dll" "$(OutDir)"</command>
+    </PostBuildEvent>
     <Manifest>
       <AdditionalManifestFiles>targetos.manifest</AdditionalManifestFiles>
     </Manifest>
@@ -347,6 +365,9 @@
       <AdditionalDependencies>posix_compat.lib;libssh.lib;openbsd_compat.lib;$(SSLLib)$(AdditionalDependentLibs);%(AdditionalDependencies)</AdditionalDependencies>
       <EntryPointSymbol>wmainCRTStartup</EntryPointSymbol>
     </Link>
+    <PostBuildEvent>
+      <command>copy /Y "$(LibreSSL-arm64-Path)\libcrypto.dll" "$(OutDir)"</command>
+    </PostBuildEvent>
     <Manifest>
       <AdditionalManifestFiles>targetos.manifest</AdditionalManifestFiles>
     </Manifest>
@@ -373,6 +394,9 @@
       <AdditionalDependencies>posix_compat.lib;libssh.lib;openbsd_compat.lib;$(SSLLib)$(AdditionalDependentLibs);%(AdditionalDependencies)</AdditionalDependencies>
       <EntryPointSymbol>wmainCRTStartup</EntryPointSymbol>
     </Link>
+    <PostBuildEvent>
+      <command>copy /Y "$(LibreSSL-arm-Path)\libcrypto.dll" "$(OutDir)"</command>
+    </PostBuildEvent>
     <Manifest>
       <AdditionalManifestFiles>targetos.manifest</AdditionalManifestFiles>
     </Manifest>
diff --git a/contrib/win32/openssh/unittest-misc.vcxproj b/contrib/win32/openssh/unittest-misc.vcxproj
index ff324c763..951b425a5 100644
--- a/contrib/win32/openssh/unittest-misc.vcxproj
+++ b/contrib/win32/openssh/unittest-misc.vcxproj
@@ -201,6 +201,9 @@
       <AdditionalDependencies>posix_compat.lib;libssh.lib;openbsd_compat.lib;$(SSLLib)$(AdditionalDependentLibs);%(AdditionalDependencies)</AdditionalDependencies>
       <EntryPointSymbol>wmainCRTStartup</EntryPointSymbol>
     </Link>
+    <PostBuildEvent>
+      <command>copy /Y "$(LibreSSL-x86-Path)\libcrypto.dll" "$(OutDir)"</command>
+    </PostBuildEvent>
     <Manifest>
       <AdditionalManifestFiles>targetos.manifest</AdditionalManifestFiles>
     </Manifest>
@@ -224,6 +227,9 @@
       <AdditionalDependencies>posix_compat.lib;libssh.lib;openbsd_compat.lib;$(SSLLib)$(AdditionalDependentLibs);%(AdditionalDependencies)</AdditionalDependencies>
       <EntryPointSymbol>wmainCRTStartup</EntryPointSymbol>
     </Link>
+    <PostBuildEvent>
+      <command>copy /Y "$(LibreSSL-x64-Path)\libcrypto.dll" "$(OutDir)"</command>
+    </PostBuildEvent>
     <Manifest>
       <AdditionalManifestFiles>targetos.manifest</AdditionalManifestFiles>
     </Manifest>
@@ -247,6 +253,9 @@
       <AdditionalDependencies>posix_compat.lib;libssh.lib;openbsd_compat.lib;$(SSLLib)$(AdditionalDependentLibs);%(AdditionalDependencies)</AdditionalDependencies>
       <EntryPointSymbol>wmainCRTStartup</EntryPointSymbol>
     </Link>
+    <PostBuildEvent>
+      <command>copy /Y "$(LibreSSL-arm64-Path)\libcrypto.dll" "$(OutDir)"</command>
+    </PostBuildEvent>
     <Manifest>
       <AdditionalManifestFiles>targetos.manifest</AdditionalManifestFiles>
     </Manifest>
@@ -270,6 +279,9 @@
       <AdditionalDependencies>posix_compat.lib;libssh.lib;openbsd_compat.lib;$(SSLLib)$(AdditionalDependentLibs);%(AdditionalDependencies)</AdditionalDependencies>
       <EntryPointSymbol>wmainCRTStartup</EntryPointSymbol>
     </Link>
+    <PostBuildEvent>
+      <command>copy /Y "$(LibreSSL-arm-Path)\libcrypto.dll" "$(OutDir)"</command>
+    </PostBuildEvent>
     <Manifest>
       <AdditionalManifestFiles>targetos.manifest</AdditionalManifestFiles>
     </Manifest>
@@ -295,6 +307,9 @@
       <AdditionalDependencies>posix_compat.lib;libssh.lib;openbsd_compat.lib;$(SSLLib)$(AdditionalDependentLibs);%(AdditionalDependencies)</AdditionalDependencies>
       <EntryPointSymbol>wmainCRTStartup</EntryPointSymbol>
     </Link>
+    <PostBuildEvent>
+      <command>copy /Y "$(LibreSSL-x86-Path)\libcrypto.dll" "$(OutDir)"</command>
+    </PostBuildEvent>
     <Manifest>
       <AdditionalManifestFiles>targetos.manifest</AdditionalManifestFiles>
     </Manifest>
@@ -321,6 +336,9 @@
       <AdditionalDependencies>posix_compat.lib;libssh.lib;openbsd_compat.lib;$(SSLLib)$(AdditionalDependentLibs);%(AdditionalDependencies)</AdditionalDependencies>
       <EntryPointSymbol>wmainCRTStartup</EntryPointSymbol>
     </Link>
+    <PostBuildEvent>
+      <command>copy /Y "$(LibreSSL-x64-Path)\libcrypto.dll" "$(OutDir)"</command>
+    </PostBuildEvent>
     <Manifest>
       <AdditionalManifestFiles>targetos.manifest</AdditionalManifestFiles>
     </Manifest>
@@ -347,6 +365,9 @@
       <AdditionalDependencies>posix_compat.lib;libssh.lib;openbsd_compat.lib;$(SSLLib)$(AdditionalDependentLibs);%(AdditionalDependencies)</AdditionalDependencies>
       <EntryPointSymbol>wmainCRTStartup</EntryPointSymbol>
     </Link>
+    <PostBuildEvent>
+      <command>copy /Y "$(LibreSSL-arm64-Path)\libcrypto.dll" "$(OutDir)"</command>
+    </PostBuildEvent>
     <Manifest>
       <AdditionalManifestFiles>targetos.manifest</AdditionalManifestFiles>
     </Manifest>
@@ -373,6 +394,9 @@
       <AdditionalDependencies>posix_compat.lib;libssh.lib;openbsd_compat.lib;$(SSLLib)$(AdditionalDependentLibs);%(AdditionalDependencies)</AdditionalDependencies>
       <EntryPointSymbol>wmainCRTStartup</EntryPointSymbol>
     </Link>
+    <PostBuildEvent>
+      <command>copy /Y "$(LibreSSL-arm-Path)\libcrypto.dll" "$(OutDir)"</command>
+    </PostBuildEvent>
     <Manifest>
       <AdditionalManifestFiles>targetos.manifest</AdditionalManifestFiles>
     </Manifest>
diff --git a/contrib/win32/openssh/unittest-sshbuf.vcxproj b/contrib/win32/openssh/unittest-sshbuf.vcxproj
index 2e843cd5e..efcdb539a 100644
--- a/contrib/win32/openssh/unittest-sshbuf.vcxproj
+++ b/contrib/win32/openssh/unittest-sshbuf.vcxproj
@@ -201,6 +201,9 @@
       <AdditionalDependencies>posix_compat.lib;libssh.lib;openbsd_compat.lib;$(SSLLib)$(AdditionalDependentLibs);%(AdditionalDependencies)</AdditionalDependencies>
       <EntryPointSymbol>wmainCRTStartup</EntryPointSymbol>
     </Link>
+    <PostBuildEvent>
+      <command>copy /Y "$(LibreSSL-x86-Path)\libcrypto.dll" "$(OutDir)"</command>
+    </PostBuildEvent>
     <Manifest>
       <AdditionalManifestFiles>targetos.manifest</AdditionalManifestFiles>
     </Manifest>
@@ -224,6 +227,9 @@
       <AdditionalDependencies>posix_compat.lib;libssh.lib;openbsd_compat.lib;$(SSLLib)$(AdditionalDependentLibs);%(AdditionalDependencies)</AdditionalDependencies>
       <EntryPointSymbol>wmainCRTStartup</EntryPointSymbol>
     </Link>
+    <PostBuildEvent>
+      <command>copy /Y "$(LibreSSL-x64-Path)\libcrypto.dll" "$(OutDir)"</command>
+    </PostBuildEvent>
     <Manifest>
       <AdditionalManifestFiles>targetos.manifest</AdditionalManifestFiles>
     </Manifest>
@@ -247,6 +253,9 @@
       <AdditionalDependencies>posix_compat.lib;libssh.lib;openbsd_compat.lib;$(SSLLib)$(AdditionalDependentLibs);%(AdditionalDependencies)</AdditionalDependencies>
       <EntryPointSymbol>wmainCRTStartup</EntryPointSymbol>
     </Link>
+    <PostBuildEvent>
+      <command>copy /Y "$(LibreSSL-arm64-Path)\libcrypto.dll" "$(OutDir)"</command>
+    </PostBuildEvent>
     <Manifest>
       <AdditionalManifestFiles>targetos.manifest</AdditionalManifestFiles>
     </Manifest>
@@ -270,6 +279,9 @@
       <AdditionalDependencies>posix_compat.lib;libssh.lib;openbsd_compat.lib;$(SSLLib)$(AdditionalDependentLibs);%(AdditionalDependencies)</AdditionalDependencies>
       <EntryPointSymbol>wmainCRTStartup</EntryPointSymbol>
     </Link>
+    <PostBuildEvent>
+      <command>copy /Y "$(LibreSSL-arm-Path)\libcrypto.dll" "$(OutDir)"</command>
+    </PostBuildEvent>
     <Manifest>
       <AdditionalManifestFiles>targetos.manifest</AdditionalManifestFiles>
     </Manifest>
@@ -295,6 +307,9 @@
       <AdditionalDependencies>posix_compat.lib;libssh.lib;openbsd_compat.lib;$(SSLLib)$(AdditionalDependentLibs);%(AdditionalDependencies)</AdditionalDependencies>
       <EntryPointSymbol>wmainCRTStartup</EntryPointSymbol>
     </Link>
+    <PostBuildEvent>
+      <command>copy /Y "$(LibreSSL-x86-Path)\libcrypto.dll" "$(OutDir)"</command>
+    </PostBuildEvent>
     <Manifest>
       <AdditionalManifestFiles>targetos.manifest</AdditionalManifestFiles>
     </Manifest>
@@ -321,6 +336,9 @@
       <AdditionalDependencies>posix_compat.lib;libssh.lib;openbsd_compat.lib;$(SSLLib)$(AdditionalDependentLibs);%(AdditionalDependencies)</AdditionalDependencies>
       <EntryPointSymbol>wmainCRTStartup</EntryPointSymbol>
     </Link>
+    <PostBuildEvent>
+      <command>copy /Y "$(LibreSSL-x64-Path)\libcrypto.dll" "$(OutDir)"</command>
+    </PostBuildEvent>
     <Manifest>
       <AdditionalManifestFiles>targetos.manifest</AdditionalManifestFiles>
     </Manifest>
@@ -347,6 +365,9 @@
       <AdditionalDependencies>posix_compat.lib;libssh.lib;openbsd_compat.lib;$(SSLLib)$(AdditionalDependentLibs);%(AdditionalDependencies)</AdditionalDependencies>
       <EntryPointSymbol>wmainCRTStartup</EntryPointSymbol>
     </Link>
+    <PostBuildEvent>
+      <command>copy /Y "$(LibreSSL-arm64-Path)\libcrypto.dll" "$(OutDir)"</command>
+    </PostBuildEvent>
     <Manifest>
       <AdditionalManifestFiles>targetos.manifest</AdditionalManifestFiles>
     </Manifest>
@@ -373,6 +394,9 @@
       <AdditionalDependencies>posix_compat.lib;libssh.lib;openbsd_compat.lib;$(SSLLib)$(AdditionalDependentLibs);%(AdditionalDependencies)</AdditionalDependencies>
       <EntryPointSymbol>wmainCRTStartup</EntryPointSymbol>
     </Link>
+    <PostBuildEvent>
+      <command>copy /Y "$(LibreSSL-arm-Path)\libcrypto.dll" "$(OutDir)"</command>
+    </PostBuildEvent>
     <Manifest>
       <AdditionalManifestFiles>targetos.manifest</AdditionalManifestFiles>
     </Manifest>
diff --git a/contrib/win32/openssh/unittest-sshkey.vcxproj b/contrib/win32/openssh/unittest-sshkey.vcxproj
index 97382e010..4c2fbce46 100644
--- a/contrib/win32/openssh/unittest-sshkey.vcxproj
+++ b/contrib/win32/openssh/unittest-sshkey.vcxproj
@@ -205,7 +205,8 @@
       <AdditionalManifestFiles>targetos.manifest</AdditionalManifestFiles>
     </Manifest>
     <PostBuildEvent>
-      <Command>xcopy /Y "$(ProjectDir)..\..\..\regress\unittests\sshkey\testdata\*" "$(OutDir)"</Command>
+      <Command>xcopy /Y "$(ProjectDir)..\..\..\regress\unittests\sshkey\testdata\*" "$(OutDir)"
+copy /Y "$(LibreSSL-x86-Path)\libcrypto.dll" "$(OutDir)"</Command>
     </PostBuildEvent>
   </ItemDefinitionGroup>
   <ItemDefinitionGroup Condition="'$(Configuration)|$(Platform)'=='Debug|x64'">
@@ -231,7 +232,8 @@
       <AdditionalManifestFiles>targetos.manifest</AdditionalManifestFiles>
     </Manifest>
     <PostBuildEvent>
-      <Command>xcopy /Y "$(ProjectDir)..\..\..\regress\unittests\sshkey\testdata\*" "$(OutDir)"</Command>
+      <Command>xcopy /Y "$(ProjectDir)..\..\..\regress\unittests\sshkey\testdata\*" "$(OutDir)"
+copy /Y "$(LibreSSL-x64-Path)\libcrypto.dll" "$(OutDir)"</Command>
     </PostBuildEvent>
   </ItemDefinitionGroup>
   <ItemDefinitionGroup Condition="'$(Configuration)|$(Platform)'=='Debug|ARM64'">
@@ -257,7 +259,8 @@
       <AdditionalManifestFiles>targetos.manifest</AdditionalManifestFiles>
     </Manifest>
     <PostBuildEvent>
-      <Command>xcopy /Y "$(ProjectDir)..\..\..\regress\unittests\sshkey\testdata\*" "$(OutDir)"</Command>
+      <Command>xcopy /Y "$(ProjectDir)..\..\..\regress\unittests\sshkey\testdata\*" "$(OutDir)"
+copy /Y "$(LibreSSL-arm64-Path)\libcrypto.dll" "$(OutDir)"</Command>
     </PostBuildEvent>
   </ItemDefinitionGroup>
   <ItemDefinitionGroup Condition="'$(Configuration)|$(Platform)'=='Debug|ARM'">
@@ -283,7 +286,8 @@
       <AdditionalManifestFiles>targetos.manifest</AdditionalManifestFiles>
     </Manifest>
     <PostBuildEvent>
-      <Command>xcopy /Y "$(ProjectDir)..\..\..\regress\unittests\sshkey\testdata\*" "$(OutDir)"</Command>
+      <Command>xcopy /Y "$(ProjectDir)..\..\..\regress\unittests\sshkey\testdata\*" "$(OutDir)"
+copy /Y "$(LibreSSL-arm-Path)\libcrypto.dll" "$(OutDir)"</Command>
     </PostBuildEvent>
   </ItemDefinitionGroup>
   <ItemDefinitionGroup Condition="'$(Configuration)|$(Platform)'=='Release|Win32'">
@@ -311,7 +315,8 @@
       <AdditionalManifestFiles>targetos.manifest</AdditionalManifestFiles>
     </Manifest>
     <PostBuildEvent>
-      <Command>xcopy /Y "$(ProjectDir)..\..\..\regress\unittests\sshkey\testdata\*" "$(OutDir)"</Command>
+      <Command>xcopy /Y "$(ProjectDir)..\..\..\regress\unittests\sshkey\testdata\*" "$(OutDir)"
+copy /Y "$(LibreSSL-x86-Path)\libcrypto.dll" "$(OutDir)"</Command>
     </PostBuildEvent>
   </ItemDefinitionGroup>
   <ItemDefinitionGroup Condition="'$(Configuration)|$(Platform)'=='Release|x64'">
@@ -340,7 +345,8 @@
       <AdditionalManifestFiles>targetos.manifest</AdditionalManifestFiles>
     </Manifest>
     <PostBuildEvent>
-      <Command>xcopy /Y "$(ProjectDir)..\..\..\regress\unittests\sshkey\testdata\*" "$(OutDir)"</Command>
+      <Command>xcopy /Y "$(ProjectDir)..\..\..\regress\unittests\sshkey\testdata\*" "$(OutDir)"
+copy /Y "$(LibreSSL-x64-Path)\libcrypto.dll" "$(OutDir)"</Command>
     </PostBuildEvent>
   </ItemDefinitionGroup>
   <ItemDefinitionGroup Condition="'$(Configuration)|$(Platform)'=='Release|ARM64'">
@@ -369,7 +375,8 @@
       <AdditionalManifestFiles>targetos.manifest</AdditionalManifestFiles>
     </Manifest>
     <PostBuildEvent>
-      <Command>xcopy /Y "$(ProjectDir)..\..\..\regress\unittests\sshkey\testdata\*" "$(OutDir)"</Command>
+      <Command>xcopy /Y "$(ProjectDir)..\..\..\regress\unittests\sshkey\testdata\*" "$(OutDir)"
+copy /Y "$(LibreSSL-arm64-Path)\libcrypto.dll" "$(OutDir)"</Command>
     </PostBuildEvent>
   </ItemDefinitionGroup>
   <ItemDefinitionGroup Condition="'$(Configuration)|$(Platform)'=='Release|ARM'">
@@ -398,7 +405,8 @@
       <AdditionalManifestFiles>targetos.manifest</AdditionalManifestFiles>
     </Manifest>
     <PostBuildEvent>
-      <Command>xcopy /Y "$(ProjectDir)..\..\..\regress\unittests\sshkey\testdata\*" "$(OutDir)"</Command>
+      <Command>xcopy /Y "$(ProjectDir)..\..\..\regress\unittests\sshkey\testdata\*" "$(OutDir)"
+copy /Y "$(LibreSSL-arm-Path)\libcrypto.dll" "$(OutDir)"</Command>
     </PostBuildEvent>
   </ItemDefinitionGroup>
   <ItemGroup>
diff --git a/contrib/win32/openssh/unittest-win32compat.vcxproj b/contrib/win32/openssh/unittest-win32compat.vcxproj
index 12d682d9d..98889948f 100644
--- a/contrib/win32/openssh/unittest-win32compat.vcxproj
+++ b/contrib/win32/openssh/unittest-win32compat.vcxproj
@@ -233,6 +233,9 @@
       <AdditionalDependencies>posix_compat.lib;libssh.lib;openbsd_compat.lib;$(SSLLib)$(AdditionalDependentLibs);%(AdditionalDependencies)</AdditionalDependencies>
       <EntryPointSymbol>wmainCRTStartup</EntryPointSymbol>
     </Link>
+    <PostBuildEvent>
+      <command>copy /Y "$(LibreSSL-x86-Path)\libcrypto.dll" "$(OutDir)"</command>
+    </PostBuildEvent>
     <Manifest>
       <AdditionalManifestFiles>targetos.manifest</AdditionalManifestFiles>
     </Manifest>
@@ -256,6 +259,9 @@
       <AdditionalDependencies>posix_compat.lib;libssh.lib;openbsd_compat.lib;$(SSLLib)$(AdditionalDependentLibs);%(AdditionalDependencies)</AdditionalDependencies>
       <EntryPointSymbol>wmainCRTStartup</EntryPointSymbol>
     </Link>
+    <PostBuildEvent>
+      <command>copy /Y "$(LibreSSL-x64-Path)\libcrypto.dll" "$(OutDir)"</command>
+    </PostBuildEvent>
     <Manifest>
       <AdditionalManifestFiles>targetos.manifest</AdditionalManifestFiles>
     </Manifest>
@@ -279,6 +285,9 @@
       <AdditionalDependencies>posix_compat.lib;libssh.lib;openbsd_compat.lib;$(SSLLib)$(AdditionalDependentLibs);%(AdditionalDependencies)</AdditionalDependencies>
       <EntryPointSymbol>wmainCRTStartup</EntryPointSymbol>
     </Link>
+    <PostBuildEvent>
+      <command>copy /Y "$(LibreSSL-arm64-Path)\libcrypto.dll" "$(OutDir)"</command>
+    </PostBuildEvent>
     <Manifest>
       <AdditionalManifestFiles>targetos.manifest</AdditionalManifestFiles>
     </Manifest>
@@ -302,6 +311,9 @@
       <AdditionalDependencies>posix_compat.lib;libssh.lib;openbsd_compat.lib;$(SSLLib)$(AdditionalDependentLibs);%(AdditionalDependencies)</AdditionalDependencies>
       <EntryPointSymbol>wmainCRTStartup</EntryPointSymbol>
     </Link>
+    <PostBuildEvent>
+      <command>copy /Y "$(LibreSSL-arm-Path)\libcrypto.dll" "$(OutDir)"</command>
+    </PostBuildEvent>
     <Manifest>
       <AdditionalManifestFiles>targetos.manifest</AdditionalManifestFiles>
     </Manifest>
@@ -327,6 +339,9 @@
       <AdditionalDependencies>posix_compat.lib;libssh.lib;openbsd_compat.lib;$(SSLLib)$(AdditionalDependentLibs);%(AdditionalDependencies)</AdditionalDependencies>
       <EntryPointSymbol>wmainCRTStartup</EntryPointSymbol>
     </Link>
+    <PostBuildEvent>
+      <command>copy /Y "$(LibreSSL-x86-Path)\libcrypto.dll" "$(OutDir)"</command>
+    </PostBuildEvent>
     <Manifest>
       <AdditionalManifestFiles>targetos.manifest</AdditionalManifestFiles>
     </Manifest>
@@ -353,6 +368,9 @@
       <AdditionalDependencies>posix_compat.lib;libssh.lib;openbsd_compat.lib;$(SSLLib)$(AdditionalDependentLibs);%(AdditionalDependencies)</AdditionalDependencies>
       <EntryPointSymbol>wmainCRTStartup</EntryPointSymbol>
     </Link>
+    <PostBuildEvent>
+      <command>copy /Y "$(LibreSSL-x64-Path)\libcrypto.dll" "$(OutDir)"</command>
+    </PostBuildEvent>
     <Manifest>
       <AdditionalManifestFiles>targetos.manifest</AdditionalManifestFiles>
     </Manifest>
@@ -379,6 +397,9 @@
       <AdditionalDependencies>posix_compat.lib;libssh.lib;openbsd_compat.lib;$(SSLLib)$(AdditionalDependentLibs);%(AdditionalDependencies)</AdditionalDependencies>
       <EntryPointSymbol>wmainCRTStartup</EntryPointSymbol>
     </Link>
+    <PostBuildEvent>
+      <command>copy /Y "$(LibreSSL-arm64-Path)\libcrypto.dll" "$(OutDir)"</command>
+    </PostBuildEvent>
     <Manifest>
       <AdditionalManifestFiles>targetos.manifest</AdditionalManifestFiles>
     </Manifest>
@@ -405,6 +426,9 @@
       <AdditionalDependencies>posix_compat.lib;libssh.lib;openbsd_compat.lib;$(SSLLib)$(AdditionalDependentLibs);%(AdditionalDependencies)</AdditionalDependencies>
       <EntryPointSymbol>wmainCRTStartup</EntryPointSymbol>
     </Link>
+    <PostBuildEvent>
+      <command>copy /Y "$(LibreSSL-arm-Path)\libcrypto.dll" "$(OutDir)"</command>
+    </PostBuildEvent>
     <Manifest>
       <AdditionalManifestFiles>targetos.manifest</AdditionalManifestFiles>
     </Manifest>