diff --git a/.gitignore b/.gitignore
index 81afb4a..d32d72a 100644
--- a/.gitignore
+++ b/.gitignore
@@ -1,2 +1,3 @@
 *.o
 git-crypt
+git-crypt.exe
diff --git a/Makefile b/Makefile
index 68eb9db..0c14f10 100644
--- a/Makefile
+++ b/Makefile
@@ -10,6 +10,19 @@ PREFIX ?= /usr/local
 BINDIR ?= $(PREFIX)/bin
 MANDIR ?= $(PREFIX)/share/man
 
+SYS := $(shell $(CXX) -dumpmachine)
+CYGWIN := $(findstring cygwin,$(SYS))
+MINGW32 := $(findstring mingw32,$(SYS))
+
+# https://stackoverflow.com/a/21749803/1432614
+ifdef CYGWIN
+	CXXFLAGS += -U__STRICT_ANSI__
+endif
+
+ifdef MINGW32
+	CXXFLAGS += -static
+endif
+
 ENABLE_MAN ?= no
 DOCBOOK_XSL ?= http://docbook.sourceforge.net/release/xsl/current/manpages/docbook.xsl
 
@@ -27,6 +40,10 @@ OBJFILES = \
 OBJFILES += crypto-openssl-10.o crypto-openssl-11.o
 LDFLAGS += -lcrypto
 
+ifdef MINGW32
+	LDFLAGS += -lgdi32
+endif
+
 XSLTPROC ?= xsltproc
 DOCBOOK_FLAGS += --param man.output.in.separate.dir 1 \
 		 --stringparam man.output.base.dir man/ \
@@ -67,7 +84,7 @@ CLEAN_TARGETS := clean-bin $(CLEAN_MAN_TARGETS-$(ENABLE_MAN))
 clean: $(CLEAN_TARGETS)
 
 clean-bin:
-	rm -f $(OBJFILES) git-crypt
+	rm -f $(OBJFILES) git-crypt git-crypt.exe
 
 clean-man:
 	rm -f man/man1/git-crypt.1
diff --git a/util-win32.cpp b/util-win32.cpp
index 4c47a2d..6965c48 100644
--- a/util-win32.cpp
+++ b/util-win32.cpp
@@ -170,6 +170,7 @@ static void	init_std_streams_platform ()
 {
 	_setmode(_fileno(stdin), _O_BINARY);
 	_setmode(_fileno(stdout), _O_BINARY);
+	std::cout.setf(std::ios::unitbuf);
 }
 
 void create_protected_file (const char* path) // TODO
diff --git a/util.cpp b/util.cpp
index 4e1aa78..75bdf7b 100644
--- a/util.cpp
+++ b/util.cpp
@@ -150,7 +150,7 @@ void		init_std_streams ()
 	init_std_streams_platform();
 }
 
-#ifdef _WIN32
+#if defined(_WIN32) && !defined(__CYGWIN__)
 #include "util-win32.cpp"
 #else
 #include "util-unix.cpp"