diff --git a/.github/workflows/msys2.yml b/.github/workflows/msys2.yml
new file mode 100644
index 000000000..0641a3104
--- /dev/null
+++ b/.github/workflows/msys2.yml
@@ -0,0 +1,41 @@
+name: MSYS2 Build Test
+
+# START OF COMMON SECTION
+on:
+  push:
+    branches: [ 'master', 'main', 'release/**' ]
+  pull_request:
+    branches: [ '*' ]
+
+concurrency:
+  group: ${{ github.workflow }}-${{ github.ref }}
+  cancel-in-progress: true
+# END OF COMMON SECTION
+
+jobs:
+  msys2:
+    runs-on: windows-latest
+    defaults:
+      run:
+        shell: msys2 {0}
+    strategy:
+      fail-fast: false
+      matrix:
+        include:
+          - { sys: ucrt64,  compiler: mingw-w64-ucrt-x86_64-gcc }
+          - { sys: mingw64, compiler: mingw-w64-x86_64-gcc }
+          - { sys: msys, compiler: gcc }
+    steps:
+      - uses: actions/checkout@v3
+      - uses: msys2/setup-msys2@v2
+        with:
+          msystem: ${{ matrix.sys }}
+          update: true
+          install: git ${{matrix.compiler}} autotools base-devel autoconf netcat
+      - name: configure wolfSSL
+        run: ./autogen.sh && ./configure CFLAGS="-DUSE_CERT_BUFFERS_2048 -DUSE_CERT_BUFFERS_256 -DNO_WRITE_TEMP_FILES"
+      - name: build wolfSSL
+        run: make check
+      - name: Display log
+        if: always()
+        run: cat test-suite.log
diff --git a/scripts/ocsp-stapling.test b/scripts/ocsp-stapling.test
index 8065ac2c6..2d544da1b 100755
--- a/scripts/ocsp-stapling.test
+++ b/scripts/ocsp-stapling.test
@@ -448,7 +448,8 @@ generate_port() {
     # Generate a random port number
     #-------------------------------------------------------------------------#
 
-    if [[ "$OSTYPE" == "linux"* ]]; then
+    if [[ "$OSTYPE" == "linux"* || "$OSTYPE" == "msys"
+                                || "$OSTYPE" == "cygwin"* ]]; then
         port=$(($(od -An -N2 /dev/urandom) % (65535-49512) + 49512))
     elif [[ "$OSTYPE" == "darwin"* ]]; then
         port=$(($(od -An -N2 /dev/random) % (65535-49512) + 49512))
diff --git a/scripts/ocsp-stapling2.test b/scripts/ocsp-stapling2.test
index dea1af61b..c5664b37a 100755
--- a/scripts/ocsp-stapling2.test
+++ b/scripts/ocsp-stapling2.test
@@ -467,7 +467,8 @@ generate_port() {
     # Generate a random port number
     #-------------------------------------------------------------------------#
 
-    if [[ "$OSTYPE" == "linux"* ]]; then
+    if [[ "$OSTYPE" == "linux"* || "$OSTYPE" == "msys"
+                                || "$OSTYPE" == "cygwin" ]]; then
         port=$(($(od -An -N2 /dev/urandom) % (65535-49512) + 49512))
     elif [[ "$OSTYPE" == "darwin"* ]]; then
         port=$(($(od -An -N2 /dev/random) % (65535-49512) + 49512))
diff --git a/tests/api.c b/tests/api.c
index 6b6596bcf..5da87ffe1 100644
--- a/tests/api.c
+++ b/tests/api.c
@@ -8242,7 +8242,7 @@ done:
     if (!sharedCtx)
         wolfSSL_CTX_free(ctx);
 
-    if (clientfd >= 0)
+    if (clientfd != SOCKET_INVALID)
         CloseSocket(clientfd);
 
 #ifdef WOLFSSL_TIRTOS
@@ -52614,7 +52614,7 @@ static int test_wolfSSL_BIO(void)
         ExpectIntEQ((int)BIO_set_mem_eof_return(f_bio1, -1), 0);
         ExpectIntEQ((int)BIO_set_mem_eof_return(NULL, -1),   0);
 
-        ExpectTrue((f1 = XFOPEN(svrCertFile, "rwb")) != XBADFILE);
+        ExpectTrue((f1 = XFOPEN(svrCertFile, "rb+")) != XBADFILE);
         ExpectIntEQ((int)BIO_set_fp(f_bio1, f1, BIO_CLOSE), WOLFSSL_SUCCESS);
         ExpectIntEQ(BIO_write_filename(f_bio2, testFile),
                 WOLFSSL_SUCCESS);
@@ -52638,7 +52638,7 @@ static int test_wolfSSL_BIO(void)
         BIO_free(f_bio2);
         f_bio2 = NULL;
 
-        ExpectNotNull(f_bio1 = BIO_new_file(svrCertFile, "rwb"));
+        ExpectNotNull(f_bio1 = BIO_new_file(svrCertFile, "rb+"));
         ExpectIntEQ((int)BIO_set_mem_eof_return(f_bio1, -1), 0);
         ExpectIntEQ(BIO_read(f_bio1, cert, sizeof(cert)), sizeof(cert));
         BIO_free(f_bio1);
@@ -55290,7 +55290,7 @@ static int test_wc_ERR_print_errors_fp(void)
     XFILE fp = XBADFILE;
 
     WOLFSSL_ERROR(WC_NO_ERR_TRACE(BAD_FUNC_ARG));
-    ExpectTrue((fp = XFOPEN("./tests/test-log-dump-to-file.txt", "ar")) !=
+    ExpectTrue((fp = XFOPEN("./tests/test-log-dump-to-file.txt", "a+")) !=
         XBADFILE);
     wc_ERR_print_errors_fp(fp);
 #if defined(DEBUG_WOLFSSL)
@@ -85971,7 +85971,8 @@ static int test_dtls_msg_from_other_peer(void)
         *  !defined(SINGLE_THREADED) && !defined(NO_RSA) */
 #if defined(WOLFSSL_DTLS) && !defined(WOLFSSL_IPV6) &&               \
     !defined(NO_WOLFSSL_CLIENT) && !defined(NO_WOLFSSL_SERVER) &&   \
-    defined(HAVE_IO_TESTS_DEPENDENCIES) && !defined(WOLFSSL_NO_TLS12)
+    defined(HAVE_IO_TESTS_DEPENDENCIES) && !defined(WOLFSSL_NO_TLS12) \
+    && !defined(USE_WINDOWS_API)
 static int test_dtls_ipv6_check(void)
 {
     EXPECT_DECLS;