diff --git a/.gitignore b/.gitignore
index 650351389d4c53..33c645e3feb81f 100644
--- a/.gitignore
+++ b/.gitignore
@@ -1,7 +1,6 @@
 /GIT-BUILD-OPTIONS
 /GIT-CFLAGS
 /GIT-LDFLAGS
-/GIT-MSVC-GEN
 /GIT-PREFIX
 /GIT-PERL-DEFINES
 /GIT-PERL-HEADER
diff --git a/Makefile b/Makefile
index eeb33bbacbf531..d1ff76ac3ac82a 100644
--- a/Makefile
+++ b/Makefile
@@ -2602,9 +2602,6 @@ ifdef GIT_INTEROP_MAKE_OPTS
 endif
 ifdef TEST_GIT_INDEX_VERSION
 	@echo TEST_GIT_INDEX_VERSION=\''$(subst ','\'',$(subst ','\'',$(TEST_GIT_INDEX_VERSION)))'\' >>$@+
-endif
-ifdef MSVC_DEPS
-	@echo MSVC_DEPS=\''$(subst ','\'',$(subst ','\'',$(MSVC_DEPS)))'\' >>$@+
 endif
 	@if cmp $@+ $@ >/dev/null 2>&1; then $(RM) $@+; else mv $@+ $@; fi
 
@@ -2754,8 +2751,6 @@ install: all
 	$(INSTALL) -m 644 $(SCRIPT_LIB) '$(DESTDIR_SQ)$(gitexec_instdir_SQ)'
 	$(INSTALL) $(install_bindir_programs) '$(DESTDIR_SQ)$(bindir_SQ)'
 ifdef MSVC
-	$(INSTALL) compat/vcbuild/GEN.DEPS/bin/*.dll '$(DESTDIR_SQ)$(bindir_SQ)'
-	$(INSTALL) compat/vcbuild/GEN.DEPS/bin/*.pdb '$(DESTDIR_SQ)$(bindir_SQ)'
 	# We DO NOT install the individual foo.o.pdb files because they
 	# have already been rolled up into the exe's pdb file.
 	# We DO NOT have pdb files for the builtin commands (like git-status.exe)
@@ -2978,9 +2973,15 @@ endif
 ifdef MSVC
 	$(RM) $(patsubst %.o,%.o.pdb,$(OBJECTS))
 	$(RM) $(patsubst %.exe,%.pdb,$(OTHER_PROGRAMS))
+	$(RM) $(patsubst %.exe,%.iobj,$(OTHER_PROGRAMS))
+	$(RM) $(patsubst %.exe,%.ipdb,$(OTHER_PROGRAMS))
 	$(RM) $(patsubst %.exe,%.pdb,$(PROGRAMS))
+	$(RM) $(patsubst %.exe,%.iobj,$(PROGRAMS))
+	$(RM) $(patsubst %.exe,%.ipdb,$(PROGRAMS))
 	$(RM) $(patsubst %.exe,%.pdb,$(TEST_PROGRAMS))
-	$(RM) GIT-MSVC-GEN
+	$(RM) $(patsubst %.exe,%.iobj,$(TEST_PROGRAMS))
+	$(RM) $(patsubst %.exe,%.ipdb,$(TEST_PROGRAMS))
+	$(RM) compat/vcbuild/MSVC-DEFS-GEN
 endif
 
 .PHONY: all install profile-clean cocciclean clean strip
diff --git a/compat/vcbuild/.gitignore b/compat/vcbuild/.gitignore
index e14691508ec6b5..8f8b794ef39f75 100644
--- a/compat/vcbuild/.gitignore
+++ b/compat/vcbuild/.gitignore
@@ -1 +1,3 @@
-GEN.*
+/vcpkg/
+/MSVC-DEFS-GEN
+/VCPKG-DEFS
diff --git a/compat/vcbuild/README b/compat/vcbuild/README
index 60fd873fe801da..2ea3da97f4087f 100644
--- a/compat/vcbuild/README
+++ b/compat/vcbuild/README
@@ -1,3 +1,54 @@
+The Steps to Build Git with VS2015 or VS2017 from the command line.
+
+1. Install the "vcpkg" open source package manager and build essential
+   third-party libaries.  The steps for this have been captured in a
+   set of convenience scripts.  These can be run from a stock Command
+   Prompt or from an SDK bash window:
+
+   $ cd <repo_root>
+   $ ./compat/vcbuild/vcpkg_install.bat
+
+   The vcpkg tools and all of the third-party sources will be installed
+   in this folder:
+      <repo_root>/compat/vcbuild/vcpkg/
+
+   A file will be created with a set of Makefile macros pointing to a
+   unified "include", "lib", and "bin" directory (release and debug) for
+   all of the required packages.  This file will be included by the main
+   Makefile:
+      <repo_root>/compat/vcbuild/MSVC-DEFS-GEN
+
+2. OPTIONALLY copy the third-party *.dll and *.pdb files into the repo
+   root to make it easier to run and debug git.exe without having to
+   manipulate your PATH.  This is especially true for debug sessions in
+   Visual Studio.
+
+   Use ONE of the following forms which should match how you want to
+   compile git.exe.
+
+   $ ./compat/vcbuild/vcpkg_copy_packages.bat debug
+   $ ./compat/vcbuild/vcpkg_copy_packages.bat release
+
+3. Build git using MSVC from an SDK bash window using one of the
+   following commands:
+
+   $ make MSVC=1
+   $ make MSVC=1 DEBUG=1
+
+================================================================
+
+Alternatively, run `make MSVC=1 vcxproj` and then load the generated
+git.sln in Visual Studio. The initial build will install the vcpkg
+system and build the dependencies automatically. This will take a while.
+
+Note that this will automatically add and commit the generated
+.sln and .vcxproj files to the repo.  You may want to drop this
+commit before submitting a Pull Request....
+
+Or maybe we should put the .sln/.vcxproj files in the .gitignores
+and not do this.  I'm not sure.
+
+================================================================
 The Steps of Build Git with VS2008
 
 1. You need the build environment, which contains the Git dependencies
diff --git a/compat/vcbuild/find_vs_env.bat b/compat/vcbuild/find_vs_env.bat
index 3800e9bf180bbf..1232f200f7dcd7 100644
--- a/compat/vcbuild/find_vs_env.bat
+++ b/compat/vcbuild/find_vs_env.bat
@@ -25,7 +25,7 @@ REM
 REM The output of this script should be written to a make "include
 REM file" and referenced by the top-level Makefile.
 REM
-REM See "config.mak.uname" (look for GIT-MSVC-GEN).
+REM See "config.mak.uname" (look for compat/vcbuild/MSVC-DEFS-GEN).
 REM ================================================================
 REM The provided command prompts are custom to each VS release and
 REM filled with lots of internal knowledge (such as Registry settings);
@@ -154,7 +154,9 @@ REM ================================================================
    REM Include DOS-style and BASH-style path for bin dir.
 
    echo msvc_bin_dir=%msvc_bin_dir%
-   echo msvc_bin_dir_msys=%msvc_bin_dir:C:=/C%
+   SET X1=%msvc_bin_dir:C:=/C%
+   SET X2=%X1:\=/%
+   echo msvc_bin_dir_msys=%X2%
 
    echo msvc_includes=%msvc_includes%
    echo msvc_libs=%msvc_libs%
diff --git a/compat/vcbuild/scripts/clink.pl b/compat/vcbuild/scripts/clink.pl
index b67b8313043352..3d6fa21c1e5690 100755
--- a/compat/vcbuild/scripts/clink.pl
+++ b/compat/vcbuild/scripts/clink.pl
@@ -14,8 +14,15 @@
 my @cflags = ();
 my @lflags = ();
 my $is_linking = 0;
+my $is_debug = 0;
 while (@ARGV) {
 	my $arg = shift @ARGV;
+	if ("$arg" eq "-DDEBUG") {
+	    # Some vcpkg-based libraries have different names for release
+	    # and debug versions.  This hack assumes that -DDEBUG comes
+	    # before any "-l*" flags.
+	    $is_debug = 1;
+	}
 	if ("$arg" =~ /^-[DIMGOZ]/) {
 		push(@cflags, $arg);
 	} elsif ("$arg" eq "-o") {
@@ -30,9 +37,13 @@
 			push(@args, "-Fd$file_out.pdb");
 		}
 	} elsif ("$arg" eq "-lz") {
+	    if ($is_debug) {
+		push(@args, "zlibd.lib");
+	    } else{
 		push(@args, "zlib.lib");
+	    }
 	} elsif ("$arg" eq "-liconv") {
-		push(@args, "iconv.lib");
+		push(@args, "libiconv.lib");
 	} elsif ("$arg" eq "-lcrypto") {
 		push(@args, "libeay32.lib");
 	} elsif ("$arg" eq "-lssl") {
@@ -40,7 +51,7 @@
 	} elsif ("$arg" eq "-lcurl") {
 		push(@args, "libcurl.lib");
 	} elsif ("$arg" eq "-lexpat") {
-		push(@args, "libexpat.lib");
+		push(@args, "expat.lib");
 	} elsif ("$arg" =~ /^-L/ && "$arg" ne "-LTCG") {
 		$arg =~ s/^-L/-LIBPATH:/;
 		push(@lflags, $arg);
diff --git a/compat/vcbuild/vcpkg_copy_dlls.bat b/compat/vcbuild/vcpkg_copy_dlls.bat
new file mode 100644
index 00000000000000..13661c14f8705c
--- /dev/null
+++ b/compat/vcbuild/vcpkg_copy_dlls.bat
@@ -0,0 +1,39 @@
+@ECHO OFF
+REM ================================================================
+REM This script is an optional step. It copies the *.dll and *.pdb
+REM files (created by vcpkg_install.bat) into the top-level directory
+REM of the repo so that you can type "./git.exe" and find them without
+REM having to fixup your PATH.
+REM
+REM NOTE: Because the names of some DLL files change between DEBUG and
+REM NOTE: RELEASE builds when built using "vcpkg.exe", you will need
+REM NOTE: to copy up the corresponding version.
+REM ================================================================
+
+	SETLOCAL EnableDelayedExpansion
+
+	@FOR /F "delims=" %%D IN ("%~dp0") DO @SET cwd=%%~fD
+	cd %cwd%
+
+	SET arch=x64-windows
+	SET inst=%cwd%vcpkg\installed\%arch%
+
+	IF [%1]==[release] (
+		echo Copying RELEASE mode DLLs to repo root...
+	) ELSE IF [%1]==[debug] (
+		SET inst=%inst%\debug
+		echo Copying DEBUG mode DLLs to repo root...
+	) ELSE (
+		echo ERROR: Invalid argument.
+		echo Usage: %~0 release
+		echo Usage: %~0 debug
+		EXIT /B 1
+	)
+
+	xcopy /e/s/v/y %inst%\bin\*.dll ..\..\
+	xcopy /e/s/v/y %inst%\bin\*.pdb ..\..\
+
+	xcopy /e/s/v/y %inst%\bin\*.dll ..\..\t\helper\
+	xcopy /e/s/v/y %inst%\bin\*.pdb ..\..\t\helper\
+
+	EXIT /B 0
diff --git a/compat/vcbuild/vcpkg_install.bat b/compat/vcbuild/vcpkg_install.bat
new file mode 100644
index 00000000000000..3d086c39c31a53
--- /dev/null
+++ b/compat/vcbuild/vcpkg_install.bat
@@ -0,0 +1,81 @@
+@ECHO OFF
+REM ================================================================
+REM This script installs the "vcpkg" source package manager and uses
+REM it to build the third-party libraries that git requires when it
+REM is built using MSVC.
+REM
+REM [1] Install VCPKG.
+REM     [a] Create <root>/compat/vcbuild/vcpkg/
+REM     [b] Download "vcpkg".
+REM     [c] Compile using the currently installed version of VS.
+REM     [d] Create <root>/compat/vcbuild/vcpkg/vcpkg.exe
+REM
+REM [2] Install third-party libraries.
+REM     [a] Download each (which may also install CMAKE).
+REM     [b] Compile in RELEASE mode and install in:
+REM         vcpkg/installed/<arch>/{bin,lib}
+REM     [c] Compile in DEBUG mode and install in:
+REM         vcpkg/installed/<arch>/debug/{bin,lib}
+REM     [d] Install headers in:
+REM         vcpkg/installed/<arch>/include
+REM
+REM [3] Create a set of MAKE definitions for the top-level
+REM     Makefile to allow "make MSVC=1" to find the above
+REM     third-party libraries.
+REM     [a] Write vcpkg/VCPGK-DEFS
+REM
+REM https://blogs.msdn.microsoft.com/vcblog/2016/09/19/vcpkg-a-tool-to-acquire-and-build-c-open-source-libraries-on-windows/
+REM https://github.com/Microsoft/vcpkg
+REM https://vcpkg.readthedocs.io/en/latest/
+REM ================================================================
+
+	SETLOCAL EnableDelayedExpansion
+
+	@FOR /F "delims=" %%D IN ("%~dp0") DO @SET cwd=%%~fD
+	cd %cwd%
+
+	dir vcpkg\vcpkg.exe >nul 2>nul && GOTO :install_libraries
+
+	echo Fetching vcpkg in %cwd%vcpkg
+	git.exe clone https://github.com/Microsoft/vcpkg vcpkg
+	IF ERRORLEVEL 1 ( EXIT /B 1 )
+
+	cd vcpkg
+	echo Building vcpkg
+	powershell -exec bypass scripts\bootstrap.ps1
+	IF ERRORLEVEL 1 ( EXIT /B 1 )
+
+	echo Successfully installed %cwd%vcpkg\vcpkg.exe
+
+:install_libraries
+	SET arch=x64-windows
+
+	echo Installing third-party libraries...
+	FOR %%i IN (zlib expat libiconv openssl libssh2 curl) DO (
+	    cd %cwd%vcpkg
+	    SET p="packages\%%i_%arch%"
+	    IF NOT EXIST "%p%" CALL :sub__install_one %%i
+	    IF ERRORLEVEL 1 ( EXIT /B 1 )
+	)
+
+:install_defines
+	cd %cwd%
+	SET inst=%cwd%vcpkg\installed\%arch%
+
+	echo vcpkg_inc=-I"%inst%\include">VCPKG-DEFS
+	echo vcpkg_rel_lib=-L"%inst%\lib">>VCPKG-DEFS
+	echo vcpkg_rel_bin="%inst%\bin">>VCPKG-DEFS
+	echo vcpkg_dbg_lib=-L"%inst%\debug\lib">>VCPKG-DEFS
+	echo vcpkg_dbg_bin="%inst%\debug\bin">>VCPKG-DEFS
+
+	EXIT /B 0
+
+
+:sub__install_one
+	echo     Installing package %1...
+
+	.\vcpkg.exe install %1:%arch%
+	IF ERRORLEVEL 1 ( EXIT /B 1 )
+
+	echo     Finished %1
+	goto :EOF
diff --git a/config.mak.uname b/config.mak.uname
index 493df2dd3b4d97..8a9dd5a8497aab 100644
--- a/config.mak.uname
+++ b/config.mak.uname
@@ -18,9 +18,16 @@ ifdef MSVC
 
 	# Generate and include makefile variables that point to the
 	# currently installed set of MSVC command line tools.
-GIT-MSVC-GEN: ./compat/vcbuild/find_vs_env.bat
-	@./compat/vcbuild/find_vs_env.bat | sed 's|\\|/|g' >GIT-MSVC-GEN
--include GIT-MSVC-GEN
+compat/vcbuild/MSVC-DEFS-GEN: compat/vcbuild/find_vs_env.bat
+	@"$<" | tr '\\' / >"$@"
+include compat/vcbuild/MSVC-DEFS-GEN
+
+	# See if vcpkg and the vcpkg-build versions of the third-party
+	# libraries that we use are installed.  We include the result
+	# to get $(vcpkg_*) variables defined for the Makefile.
+compat/vcbuild/VCPKG-DEFS: compat/vcbuild/vcpkg_install.bat
+	@"$<"
+include compat/vcbuild/VCPKG-DEFS
 endif
 
 # We choose to avoid "if .. else if .. else .. endif endif"
@@ -427,13 +434,13 @@ ifeq ($(uname_S),Windows)
 	EXTLIBS = user32.lib advapi32.lib shell32.lib wininet.lib ws2_32.lib invalidcontinue.obj kernel32.lib ntdll.lib
 	PTHREAD_LIBS =
 	lib =
-	# Path to the unpacked third-party libraries
-	MSVC_DEPS = compat/vcbuild/GEN.DEPS
-	BASIC_CFLAGS += \
-		     -I$(MSVC_DEPS)/include -I$(MSVC_DEPS)/include/expat -I$(MSVC_DEPS)/include/zlib \
-		     -L$(MSVC_DEPS)/lib \
-		     $(sdk_includes) $(sdk_libs) \
-		     $(msvc_includes) $(msvc_libs)
+	BASIC_CFLAGS += $(vcpkg_inc) $(sdk_includes) $(msvc_includes)
+ifndef DEBUG
+	BASIC_CFLAGS += $(vcpkg_rel_lib)
+else
+	BASIC_CFLAGS += $(vcpkg_dbg_lib)
+endif
+	BASIC_CFLAGS += $(sdk_libs) $(msvc_libs)
 
 	# Optionally enable memory leak reporting.
 	# BASIC_CLFAGS += -DUSE_MSVC_CRTDBG
diff --git a/t/test-lib.sh b/t/test-lib.sh
index 27184a41084598..90adb622645321 100644
--- a/t/test-lib.sh
+++ b/t/test-lib.sh
@@ -57,9 +57,6 @@ fi
 . "$GIT_BUILD_DIR"/GIT-BUILD-OPTIONS
 export PERL_PATH SHELL_PATH
 
-test -z "$MSVC_DEPS" ||
-PATH="$GIT_BUILD_DIR/$MSVC_DEPS/bin:$PATH"
-
 ################################################################
 # It appears that people try to run tests without building...
 "$GIT_BUILD_DIR/git$X" >/dev/null