diff --git a/.evergreen/compile.sh b/.evergreen/compile.sh
index 2973296a2e..a5148cd1b5 100755
--- a/.evergreen/compile.sh
+++ b/.evergreen/compile.sh
@@ -19,6 +19,7 @@ set -o pipefail
 : "${ENABLE_CODE_COVERAGE:-}"
 : "${ENABLE_TESTS:-}"
 : "${generator:-}"
+: "${platform:-}"
 : "${REQUIRED_CXX_STANDARD:-}"
 : "${RUN_DISTCHECK:-}"
 : "${USE_POLYFILL_BOOST:-}"
@@ -27,23 +28,6 @@ set -o pipefail
 : "${USE_SANITIZER_UBSAN:-}"
 : "${USE_STATIC_LIBS:-}"
 
-# Add MSBuild.exe to path.
-if [[ "${OSTYPE:?}" == "cygwin" ]]; then
-  case "${generator:-}" in
-  *2015*)
-    PATH="/cygdrive/c/cmake/bin:/cygdrive/c/Program Files (x86)/MSBuild/14.0/Bin:$PATH"
-    ;;
-  *2017*)
-    PATH="/cygdrive/c/cmake/bin:/cygdrive/c/Program Files (x86)/Microsoft Visual Studio/2017/Professional/MSBuild/15.0/Bin:$PATH"
-    ;;
-  *)
-    echo "missing explicit CMake Generator on Windows distro" 1>&2
-    exit 1
-    ;;
-  esac
-fi
-export PATH
-
 mongoc_prefix="$(pwd)/../mongoc"
 echo "mongoc_prefix=${mongoc_prefix:?}"
 
@@ -123,7 +107,7 @@ case "${OSTYPE:?}" in
 cygwin)
   case "${generator:-}" in
   *2015*) cmake_flags+=("-DBOOST_ROOT=C:/local/boost_1_60_0") ;;
-  *2017*) cmake_flags+=("-DCMAKE_CXX_STANDARD=17") ;;
+  *2017*|*2019*) cmake_flags+=("-DCMAKE_CXX_STANDARD=17") ;;
   *)
     echo "missing explicit CMake Generator on Windows distro" 1>&2
     exit 1
@@ -142,6 +126,7 @@ darwin* | linux*)
   ;;
 esac
 export CMAKE_GENERATOR="${generator:?}"
+export CMAKE_GENERATOR_PLATFORM="${platform:-}"
 
 if [[ "${USE_POLYFILL_STD_EXPERIMENTAL:-}" == "ON" ]]; then
   cmake_flags+=(
diff --git a/.evergreen/install_c_driver.sh b/.evergreen/install_c_driver.sh
index 1e2f777d7f..766e7cffb3 100755
--- a/.evergreen/install_c_driver.sh
+++ b/.evergreen/install_c_driver.sh
@@ -83,14 +83,17 @@ if [[ "${OSTYPE}" == darwin* ]]; then
   }
 fi
 
+
 # Default CMake generator to use if not already provided.
-declare cmake_generator
+declare CMAKE_GENERATOR CMAKE_GENERATOR_PLATFORM
 if [[ "${OSTYPE:?}" == "cygwin" ]]; then
-  cmake_generator=${generator:-"Visual Studio 14 2015 Win64"}
+  CMAKE_GENERATOR="${generator:-"Visual Studio 14 2015"}"
+  CMAKE_GENERATOR_PLATFORM="${platform:-"x64"}"
 else
-  cmake_generator=${generator:-"Unix Makefiles"}
+  CMAKE_GENERATOR="${generator:-"Unix Makefiles"}"
+  CMAKE_GENERATOR_PLATFORM="${platform:-""}"
 fi
-: "${cmake_generator:?}"
+export CMAKE_GENERATOR CMAKE_GENERATOR_PLATFORM
 
 declare -a configure_flags=(
   "-DCMAKE_BUILD_TYPE=Debug"
@@ -131,7 +134,7 @@ fi
 # Install libmongoc.
 {
   echo "Installing C Driver into ${mongoc_dir}..." 1>&2
-  "${cmake_binary}" -S "${mongoc_idir}" -B "${mongoc_idir}" -G "${cmake_generator}" "${configure_flags[@]}"
+  "${cmake_binary}" -S "${mongoc_idir}" -B "${mongoc_idir}" "${configure_flags[@]}"
   "${cmake_binary}" --build "${mongoc_idir}" --config Debug --target install -- "${compile_flags[@]}"
   echo "Installing C Driver into ${mongoc_dir}... done." 1>&2
 } >/dev/null
diff --git a/.evergreen/test.sh b/.evergreen/test.sh
index 97ae5df168..3bb32d6592 100755
--- a/.evergreen/test.sh
+++ b/.evergreen/test.sh
@@ -23,6 +23,7 @@ set -o pipefail
 : "${generator:-}"
 : "${lib_dir:-}"
 : "${MONGODB_API_VERSION:-}"
+: "${platform:-}"
 : "${TEST_WITH_ASAN:-}"
 : "${TEST_WITH_UBSAN:-}"
 : "${TEST_WITH_VALGRIND:-}"
@@ -40,23 +41,6 @@ fi
 export MONGOCRYPTD_PATH
 popd # ..
 
-# Add MSBuild.exe to path.
-if [[ "$OSTYPE" == "cygwin" ]]; then
-  case "${generator}" in
-  *2015*)
-    PATH="/cygdrive/c/cmake/bin:/cygdrive/c/Program Files (x86)/MSBuild/14.0/Bin:$PATH"
-    ;;
-  *2017*)
-    PATH="/cygdrive/c/cmake/bin:/cygdrive/c/Program Files (x86)/Microsoft Visual Studio/2017/Professional/MSBuild/15.0/Bin:$PATH"
-    ;;
-  *)
-    echo "missing explicit CMake Generator on Windows distro" 1>&2
-    exit 1
-    ;;
-  esac
-fi
-export PATH
-
 mongoc_dir="${working_dir:?}/../mongoc"
 export mongoc_dir
 
@@ -111,6 +95,12 @@ fi
 export DRIVERS_TOOLS
 popd # "${working_dir:?}/../drivers-evergreen-tools"
 
+# shellcheck source=/dev/null
+. "${mongoc_dir:?}/.evergreen/scripts/find-cmake-latest.sh"
+export cmake_binary
+cmake_binary="$(find_cmake_latest)"
+command -v "${cmake_binary:?}"
+
 export MONGOCXX_TEST_TLS_CA_FILE="${DRIVERS_TOOLS:?}/.evergreen/x509gen/ca.pem"
 
 if [ "$(uname -m)" == "ppc64le" ]; then
@@ -215,13 +205,13 @@ fi
 pushd "${working_dir:?}/build"
 
 if [[ "${OSTYPE:?}" =~ cygwin ]]; then
-  CTEST_OUTPUT_ON_FAILURE=1 MSBuild.exe /p:Configuration="${build_type:?}" /verbosity:minimal RUN_TESTS.vcxproj
+  CTEST_OUTPUT_ON_FAILURE=1 "${cmake_binary:?}" --build . --target RUN_TESTS -- /p:Configuration="${build_type:?}" /verbosity:minimal
   # Only run examples if MONGODB_API_VERSION is unset. We do not append
   # API version to example clients, so examples will fail when requireApiVersion
   # is true.
   if [[ -z "$MONGODB_API_VERSION" ]]; then
     echo "Running examples..."
-    if ! CTEST_OUTPUT_ON_FAILURE=1 MSBuild.exe /p:Configuration="${build_type:?}" /verbosity:minimal examples/run-examples.vcxproj >|output.txt 2>&1; then
+    if ! CTEST_OUTPUT_ON_FAILURE=1 "${cmake_binary:?}" --build . --target examples/run-examples -- /p:Configuration="${build_type:?}" /verbosity:minimal >|output.txt 2>&1; then
       # Only emit output on failure.
       cat output.txt 1>&2
       exit 1
@@ -324,6 +314,8 @@ fi
 export PKG_CONFIG_PATH
 
 # Environment variables used by example projects.
+export CMAKE_GENERATOR="${generator:-}"
+export CMAKE_GENERATOR_PLATFORM="${platform:-}"
 export BUILD_TYPE="${build_type:?}"
 export CXXFLAGS="${example_projects_cxxflags}"
 export LDFLAGS="${example_projects_ldflags}"
@@ -353,11 +345,6 @@ fi
 # is true.
 if [[ -z "${MONGODB_API_VERSION:-}" ]]; then
   echo "Building example projects..."
-  # shellcheck source=/dev/null
-  . "${mongoc_dir:?}/.evergreen/scripts/find-cmake-latest.sh"
-  export cmake_binary
-  cmake_binary="$(find_cmake_latest)"
-  command -v "${cmake_binary:?}"
   .evergreen/build_example_projects.sh
   echo "Building example projects... done."
 fi
diff --git a/.mci.yml b/.mci.yml
index dbde7d36ea..b0df280423 100644
--- a/.mci.yml
+++ b/.mci.yml
@@ -40,9 +40,15 @@ variables:
         integration_matrix_expansions_linux: &integration_matrix_expansions_linux
             build_type: "Debug"
             ENABLE_CODE_COVERAGE: ON
-        integration_matrix_expansions_windows: &integration_matrix_expansions_windows
+        integration_matrix_expansions_windows_vs2017: &integration_matrix_expansions_windows_vs2017
             build_type: "Debug" # Same for Windows and Linux
-            generator: Visual Studio 15 2017 Win64
+            generator: Visual Studio 15 2017
+            platform: x64
+            example_projects_cxx_standard: 17
+        integration_matrix_expansions_windows_vs2019: &integration_matrix_expansions_windows_vs2019
+            build_type: "Debug" # Same for Windows and Linux
+            generator: Visual Studio 16 2019
+            platform: x64
             example_projects_cxx_standard: 17
 
 #######################################
@@ -348,6 +354,7 @@ functions:
                   - ENABLE_CODE_COVERAGE
                   - ENABLE_TESTS
                   - generator
+                  - platform
                   - REQUIRED_CXX_STANDARD
                   - RUN_DISTCHECK
                   - USE_POLYFILL_BOOST
@@ -395,6 +402,7 @@ functions:
                   - generator
                   - lib_dir
                   - MONGODB_API_VERSION
+                  - platform
                   - TEST_WITH_ASAN
                   - TEST_WITH_UBSAN
                   - TEST_WITH_VALGRIND
@@ -1074,60 +1082,60 @@ buildvariants:
           <<: *integration_matrix_expansions_linux
       <<: *integration_matrix_tasks_single
 
-    - name: integration-vs2017-latest-single
-      display_name: "Windows (VS 2017) Debug (MongoDB Latest)"
-      run_on: windows-64-vs2017-large
+    - name: integration-vs2019-latest-single
+      display_name: "Windows (VS 2019) Debug (MongoDB Latest)"
+      run_on: windows-vsCurrent-large
       expansions:
           mongodb_version: "latest"
-          <<: *integration_matrix_expansions_windows
+          <<: *integration_matrix_expansions_windows_vs2019
       <<: *integration_matrix_tasks_single
 
-    - name: integration-vs2017-7.0-single
-      display_name: "Windows (VS 2017) Debug (MongoDB 7.0)"
-      run_on: windows-64-vs2017-large
+    - name: integration-vs2019-7.0-single
+      display_name: "Windows (VS 2019) Debug (MongoDB 7.0)"
+      run_on: windows-vsCurrent-large
       expansions:
           mongodb_version: "7.0"
-          <<: *integration_matrix_expansions_windows
+          <<: *integration_matrix_expansions_windows_vs2019
       <<: *integration_matrix_tasks_single
 
-    - name: integration-vs2017-6.0-single
-      display_name: "Windows (VS 2017) Debug (MongoDB 6.0)"
-      run_on: windows-64-vs2017-large
+    - name: integration-vs2019-6.0-single
+      display_name: "Windows (VS 2019) Debug (MongoDB 6.0)"
+      run_on: windows-vsCurrent-large
       expansions:
           mongodb_version: "6.0"
-          <<: *integration_matrix_expansions_windows
+          <<: *integration_matrix_expansions_windows_vs2019
       <<: *integration_matrix_tasks_single
 
-    - name: integration-vs2017-5.0-single
-      display_name: "Windows (VS 2017) Debug (MongoDB 5.0)"
-      run_on: windows-64-vs2017-large
+    - name: integration-vs2019-5.0-single
+      display_name: "Windows (VS 2019) Debug (MongoDB 5.0)"
+      run_on: windows-vsCurrent-large
       expansions:
           mongodb_version: "5.0"
-          <<: *integration_matrix_expansions_windows
+          <<: *integration_matrix_expansions_windows_vs2019
       <<: *integration_matrix_tasks_single
 
-    - name: integration-vs2017-4.4-single
-      display_name: "Windows (VS 2017) Debug (MongoDB 4.4)"
-      run_on: windows-64-vs2017-large
+    - name: integration-vs2019-4.4-single
+      display_name: "Windows (VS 2019) Debug (MongoDB 4.4)"
+      run_on: windows-vsCurrent-large
       expansions:
           mongodb_version: "4.4"
-          <<: *integration_matrix_expansions_windows
+          <<: *integration_matrix_expansions_windows_vs2019
       <<: *integration_matrix_tasks_single
 
-    - name: integration-vs2017-4.2-single
-      display_name: "Windows (VS 2017) Debug (MongoDB 4.2)"
-      run_on: windows-64-vs2017-large
+    - name: integration-vs2019-4.2-single
+      display_name: "Windows (VS 2019) Debug (MongoDB 4.2)"
+      run_on: windows-vsCurrent-large
       expansions:
           mongodb_version: "4.2"
-          <<: *integration_matrix_expansions_windows
+          <<: *integration_matrix_expansions_windows_vs2019
       <<: *integration_matrix_tasks_single
 
-    - name: integration-vs2017-4.0-single
-      display_name: "Windows (VS 2017) Debug (MongoDB 4.0)"
-      run_on: windows-64-vs2017-large
+    - name: integration-vs2019-4.0-single
+      display_name: "Windows (VS 2019) Debug (MongoDB 4.0)"
+      run_on: windows-vsCurrent-large
       expansions:
           mongodb_version: "4.0"
-          <<: *integration_matrix_expansions_windows
+          <<: *integration_matrix_expansions_windows_vs2019
       <<: *integration_matrix_tasks_single
 
     - name: integration-ubuntu2004-latest-replica
@@ -1252,10 +1260,18 @@ buildvariants:
 
     - name: integration-auth-vs2017-latest-single
       display_name: "Windows (VS 2017) Debug Latest Auth"
-      run_on: windows-64-vs2017-large
+      run_on: windows-vsCurrent-large
+      expansions:
+          mongodb_version: "latest"
+          <<: *integration_matrix_expansions_windows_vs2017
+      <<: *integration_matrix_auth_tasks_single
+
+    - name: integration-auth-vs2019-latest-single
+      display_name: "Windows (VS 2019) Debug Latest Auth"
+      run_on: windows-vsCurrent-large
       expansions:
           mongodb_version: "latest"
-          <<: *integration_matrix_expansions_windows
+          <<: *integration_matrix_expansions_windows_vs2019
       <<: *integration_matrix_auth_tasks_single
 
     - name: integration-versioned-api-ubuntu2004-latest-single
@@ -1266,12 +1282,12 @@ buildvariants:
           <<: *integration_matrix_expansions_linux
       <<: *integration_matrix_versioned_api_tasks_single
 
-    - name: integration-versioned-api-vs2017-latest-single
-      display_name: "Windows (VS 2017) Debug Latest Versioned API"
-      run_on: windows-64-vs2017-large
+    - name: integration-versioned-api-vs2019-latest-single
+      display_name: "Windows (VS 2019) Debug Latest Versioned API"
+      run_on: windows-vsCurrent-large
       expansions:
           mongodb_version: "latest"
-          <<: *integration_matrix_expansions_windows
+          <<: *integration_matrix_expansions_windows_vs2019
       <<: *integration_matrix_versioned_api_tasks_single
 
     - name: integration-mongocryptd-ubuntu2004-latest
@@ -1833,7 +1849,8 @@ buildvariants:
       expansions:
           build_type: "Release"
           mongodb_version: "4.2"
-          generator: Visual Studio 14 2015 Win64
+          generator: Visual Studio 14 2015
+          platform: x64
       run_on:
           - windows-64-vs2015-compile
       tasks:
@@ -1848,7 +1865,8 @@ buildvariants:
       expansions:
           build_type: "Debug"
           mongodb_version: "4.2"
-          generator: Visual Studio 14 2015 Win64
+          generator: Visual Studio 14 2015
+          platform: x64
       run_on:
           - windows-64-vs2015-compile
       tasks:
@@ -1860,7 +1878,8 @@ buildvariants:
       display_name: "Windows (VS 2015) Debug (MongoDB 4.2)"
       expansions:
           build_type: "Debug"
-          generator: Visual Studio 14 2015 Win64
+          generator: Visual Studio 14 2015
+          platform: x64
           mongodb_version: "4.2"
       run_on:
          - windows-64-vs2015-compile
diff --git a/docs/content/mongocxx-v3/installation/windows.md b/docs/content/mongocxx-v3/installation/windows.md
index e60d388924..6c4589d023 100644
--- a/docs/content/mongocxx-v3/installation/windows.md
+++ b/docs/content/mongocxx-v3/installation/windows.md
@@ -67,7 +67,7 @@ On Windows, the C++ driver is configured as follows (adjusting the path of the C
 
 ```sh
 'C:\Program Files (x86)\CMake\bin\cmake.exe' .. \
-     -G "Visual Studio 14 2015 Win64"           \
+     -G "Visual Studio 14 2015" -A "x64"        \
     -DBOOST_ROOT=C:\local\boost_1_60_0          \
     -DCMAKE_INSTALL_PREFIX=C:\mongo-cxx-driver
 ```
@@ -81,7 +81,7 @@ To build with Visual Studio 2017 without a C++17 polyfill, configure as follows:
 
 ```sh
 'C:\Program Files (x86)\CMake\bin\cmake.exe' .. \
-    -G "Visual Studio 15 2017 Win64"            \
+    -G "Visual Studio 15 2017" -A "x64"         \
     -DCMAKE_CXX_STANDARD=17                     \
     -DCMAKE_INSTALL_PREFIX=C:\mongo-cxx-driver  \
 ```
@@ -94,7 +94,7 @@ To build versions 3.7.0 and older without a C++17 polyfill, it is necessary to c
 
 ```sh
 'C:\Program Files (x86)\CMake\bin\cmake.exe' .. \
-    -G "Visual Studio 15 2017 Win64"            \
+    -G "Visual Studio 15 2017" -A "x64"         \
     -DCMAKE_CXX_STANDARD=17                     \
     -DCMAKE_CXX_FLAGS="/Zc:__cplusplus /EHsc"   \
     -DCMAKE_INSTALL_PREFIX=C:\mongo-cxx-driver  \
diff --git a/examples/projects/bsoncxx/cmake/shared/build.sh b/examples/projects/bsoncxx/cmake/shared/build.sh
index 3ce50b5bbe..1e86923671 100755
--- a/examples/projects/bsoncxx/cmake/shared/build.sh
+++ b/examples/projects/bsoncxx/cmake/shared/build.sh
@@ -13,10 +13,10 @@ if [ -z "$MSVC" ]; then
     "$CMAKE" --build . --target run
 else
     if [ "$CXX_STANDARD" = "17" ]; then
-        "$CMAKE" -G "Visual Studio 15 2017 Win64" -DCMAKE_CXX_STANDARD="${CXX_STANDARD}" ..
+        "$CMAKE" -G "Visual Studio 15 2017" -A "x64" -DCMAKE_CXX_STANDARD="${CXX_STANDARD}" ..
     else
         # Boost is needed for pre-17 Windows polyfill.
-        "$CMAKE" -G "Visual Studio 14 2015 Win64" -DCMAKE_CXX_STANDARD="${CXX_STANDARD}" -DBOOST_ROOT=c:/local/boost_1_60_0 ..
+        "$CMAKE" -G "Visual Studio 14 2015" -A "x64" -DCMAKE_CXX_STANDARD="${CXX_STANDARD}" -DBOOST_ROOT=c:/local/boost_1_60_0 ..
     fi
     "$CMAKE" --build . --target run --config "${BUILD_TYPE}" -- /verbosity:minimal
 fi
diff --git a/examples/projects/bsoncxx/cmake/static/build.sh b/examples/projects/bsoncxx/cmake/static/build.sh
index 3ce50b5bbe..1e86923671 100755
--- a/examples/projects/bsoncxx/cmake/static/build.sh
+++ b/examples/projects/bsoncxx/cmake/static/build.sh
@@ -13,10 +13,10 @@ if [ -z "$MSVC" ]; then
     "$CMAKE" --build . --target run
 else
     if [ "$CXX_STANDARD" = "17" ]; then
-        "$CMAKE" -G "Visual Studio 15 2017 Win64" -DCMAKE_CXX_STANDARD="${CXX_STANDARD}" ..
+        "$CMAKE" -G "Visual Studio 15 2017" -A "x64" -DCMAKE_CXX_STANDARD="${CXX_STANDARD}" ..
     else
         # Boost is needed for pre-17 Windows polyfill.
-        "$CMAKE" -G "Visual Studio 14 2015 Win64" -DCMAKE_CXX_STANDARD="${CXX_STANDARD}" -DBOOST_ROOT=c:/local/boost_1_60_0 ..
+        "$CMAKE" -G "Visual Studio 14 2015" -A "x64" -DCMAKE_CXX_STANDARD="${CXX_STANDARD}" -DBOOST_ROOT=c:/local/boost_1_60_0 ..
     fi
     "$CMAKE" --build . --target run --config "${BUILD_TYPE}" -- /verbosity:minimal
 fi
diff --git a/examples/projects/mongocxx/cmake/shared/build.sh b/examples/projects/mongocxx/cmake/shared/build.sh
index 3ce50b5bbe..1e86923671 100755
--- a/examples/projects/mongocxx/cmake/shared/build.sh
+++ b/examples/projects/mongocxx/cmake/shared/build.sh
@@ -13,10 +13,10 @@ if [ -z "$MSVC" ]; then
     "$CMAKE" --build . --target run
 else
     if [ "$CXX_STANDARD" = "17" ]; then
-        "$CMAKE" -G "Visual Studio 15 2017 Win64" -DCMAKE_CXX_STANDARD="${CXX_STANDARD}" ..
+        "$CMAKE" -G "Visual Studio 15 2017" -A "x64" -DCMAKE_CXX_STANDARD="${CXX_STANDARD}" ..
     else
         # Boost is needed for pre-17 Windows polyfill.
-        "$CMAKE" -G "Visual Studio 14 2015 Win64" -DCMAKE_CXX_STANDARD="${CXX_STANDARD}" -DBOOST_ROOT=c:/local/boost_1_60_0 ..
+        "$CMAKE" -G "Visual Studio 14 2015" -A "x64" -DCMAKE_CXX_STANDARD="${CXX_STANDARD}" -DBOOST_ROOT=c:/local/boost_1_60_0 ..
     fi
     "$CMAKE" --build . --target run --config "${BUILD_TYPE}" -- /verbosity:minimal
 fi
diff --git a/examples/projects/mongocxx/cmake/static/build.sh b/examples/projects/mongocxx/cmake/static/build.sh
index 3ce50b5bbe..1e86923671 100755
--- a/examples/projects/mongocxx/cmake/static/build.sh
+++ b/examples/projects/mongocxx/cmake/static/build.sh
@@ -13,10 +13,10 @@ if [ -z "$MSVC" ]; then
     "$CMAKE" --build . --target run
 else
     if [ "$CXX_STANDARD" = "17" ]; then
-        "$CMAKE" -G "Visual Studio 15 2017 Win64" -DCMAKE_CXX_STANDARD="${CXX_STANDARD}" ..
+        "$CMAKE" -G "Visual Studio 15 2017" -A "x64" -DCMAKE_CXX_STANDARD="${CXX_STANDARD}" ..
     else
         # Boost is needed for pre-17 Windows polyfill.
-        "$CMAKE" -G "Visual Studio 14 2015 Win64" -DCMAKE_CXX_STANDARD="${CXX_STANDARD}" -DBOOST_ROOT=c:/local/boost_1_60_0 ..
+        "$CMAKE" -G "Visual Studio 14 2015" -A "x64" -DCMAKE_CXX_STANDARD="${CXX_STANDARD}" -DBOOST_ROOT=c:/local/boost_1_60_0 ..
     fi
     "$CMAKE" --build . --target run --config "${BUILD_TYPE}" -- /verbosity:minimal
 fi