diff --git a/.github/workflows/find_openssl.bat b/.github/workflows/find_openssl.bat
new file mode 100644
index 0000000000..a1cd86b835
--- /dev/null
+++ b/.github/workflows/find_openssl.bat
@@ -0,0 +1,10 @@
+@echo off
+setlocal EnableDelayedExpansion
+REM Find every openssl.exe reachable through PATH:
+for /f "delims=" %%F in ('where openssl 2^>nul') do (
+    set "OPENSSL_DIR=%%~dpF"
+    echo OpenSSL lives in: "!OPENSSL_DIR!"
+    goto :end
+)
+echo OpenSSL not found in: "!PATH!"
+:end
diff --git a/.github/workflows/windows_ci.yml b/.github/workflows/windows_ci.yml
index 14b81470cf..4d7220d6f6 100644
--- a/.github/workflows/windows_ci.yml
+++ b/.github/workflows/windows_ci.yml
@@ -25,17 +25,35 @@ concurrency:
 
 jobs:
   gcc-windows:
-    runs-on: windows-2019
+    runs-on: windows-2025
     timeout-minutes: 90
     env:
       VFLAGS: -cc gcc
     steps:
       - uses: actions/checkout@v4
-      - name: Build
+      - name: Show tool versions
         run: |
           gcc --version
+          pkg-config --version
+          openssl version
+          echo "Flags for openssl:"
+          pkg-config openssl --cflags
+          echo "Flags for openssl libs:"
+          pkg-config openssl --libs
+          .github/workflows/find_openssl.bat
+          echo "OpenSSL files:"
+          where.exe /R "C:\Program Files\OpenSSL" *.*
+          echo "Include files for openssl:"
+          dir "c:/Program Files/OpenSSL/include"
+          echo "Lib Include files for openssl:"
+          dir "c:/Program Files/OpenSSL/lib/VC/x64/"
+      - name: Build
+        run: |
           .\make.bat -gcc
           .\v.exe symlink
+          .\v.exe -stats vlib/crypto/ecdsa/ecdsa_test.v
+      - name: Test v binaries
+        run: v -silent build-vbinaries
       - name: All code is formatted
         run: v -silent test-cleancode
       - name: Test new v.c
@@ -64,8 +82,6 @@ jobs:
         run: v -autofree vlib/v/tests/options/option_test.c.v
       - name: Test v->js
         run: v -o hi.js examples/js_hello_world.v && node hi.js
-      - name: Test v binaries
-        run: v -silent build-vbinaries
       - name: Build examples
         run: v -silent build-examples
       - name: v2 self compilation
diff --git a/cmd/tools/modules/testing/common.v b/cmd/tools/modules/testing/common.v
index d93bb4b18d..34fe57f9bb 100644
--- a/cmd/tools/modules/testing/common.v
+++ b/cmd/tools/modules/testing/common.v
@@ -46,12 +46,16 @@ pub const is_node_present = os.execute('node --version').exit_code == 0
 pub const is_go_present = os.execute('go version').exit_code == 0
 
 pub const is_ruby_present = os.execute('ruby --version').exit_code == 0
+	&& os.execute('pkg-config ruby --libs').exit_code == 0
 
 pub const is_python_present = os.execute('python --version').exit_code == 0
+	&& os.execute('pkg-config python3 --libs').exit_code == 0
 
 pub const is_sqlite3_present = os.execute('sqlite3 --version').exit_code == 0
+	&& os.execute('pkg-config sqlite3 --libs').exit_code == 0
 
 pub const is_openssl_present = os.execute('openssl --version').exit_code == 0
+	&& os.execute('pkg-config openssl --libs').exit_code == 0
 
 pub const all_processes = get_all_processes()
 
diff --git a/vlib/crypto/ecdsa/ecdsa.c.v b/vlib/crypto/ecdsa/ecdsa.c.v
index 388508f58e..38a20a5ba3 100644
--- a/vlib/crypto/ecdsa/ecdsa.c.v
+++ b/vlib/crypto/ecdsa/ecdsa.c.v
@@ -15,6 +15,14 @@ module ecdsa
 #flag linux -I/usr/local/include/openssl
 #flag linux -L/usr/local/lib64/
 
+// Installed through choco:
+#flag windows -IC:/Program Files/OpenSSL-Win64/include
+#flag windows -LC:/Program Files/OpenSSL-Win64/lib/VC/x64/MD
+
+// Installed on the CI:
+#flag windows -IC:/Program Files/OpenSSL/include
+#flag windows -LC:/Program Files/OpenSSL/lib/VC/x64/MD
+
 #flag -I/usr/include/openssl
 
 #flag -lcrypto
diff --git a/vlib/net/openssl/openssl.c.v b/vlib/net/openssl/openssl.c.v
index 8474390312..d70cda2793 100644
--- a/vlib/net/openssl/openssl.c.v
+++ b/vlib/net/openssl/openssl.c.v
@@ -14,11 +14,22 @@ module openssl
 // openssl.
 #flag freebsd -I/usr/local/include
 #flag freebsd -L/usr/local/lib
+
+// Installed through choco:
+#flag windows -IC:/Program Files/OpenSSL-Win64/include
+#flag windows -LC:/Program Files/OpenSSL-Win64/lib/VC/x64/MD
+
+// Installed on the CI:
+#flag windows -IC:/Program Files/OpenSSL/include
+#flag windows -LC:/Program Files/OpenSSL/lib/VC/x64/MD
+
 $if $pkgconfig('openssl') {
 	#pkgconfig --cflags --libs openssl
 } $else {
 	#flag windows -l libssl -l libcrypto
-	#flag -lssl -lcrypto
+	$if !windows {
+		#flag -lssl -lcrypto
+	}
 	#flag linux -ldl -lpthread
 	// MacPorts
 	#flag darwin -I/opt/local/include
diff --git a/vlib/v/gen/native/tests/native_test.v b/vlib/v/gen/native/tests/native_test.v
index 41905bf66f..6c2a4aa102 100644
--- a/vlib/v/gen/native/tests/native_test.v
+++ b/vlib/v/gen/native/tests/native_test.v
@@ -1,4 +1,4 @@
-// vtest build: (amd64 || arm64) && !self_sandboxed_packaging?
+// vtest build: (amd64 || arm64) && !self_sandboxed_packaging? && !gcc-windows
 import os
 import time
 import benchmark