diff --git a/.github/workflows/configure.yml b/.github/workflows/configure.yml
index 01eacba1f..c3edce593 100644
--- a/.github/workflows/configure.yml
+++ b/.github/workflows/configure.yml
@@ -19,7 +19,7 @@ jobs:
       matrix:
         runs-on: [ubuntu-latest, macos-latest, windows-latest]
         arch: [x64]
-        cmake: [3.18]
+        cmake: ["3.21"]
 
         include:
         - runs-on: ubuntu-latest
diff --git a/CMakeLists.txt b/CMakeLists.txt
index 84a613681..0e955df76 100644
--- a/CMakeLists.txt
+++ b/CMakeLists.txt
@@ -7,13 +7,13 @@
 
 cmake_minimum_required(VERSION 3.4)
 
-# The `cmake_minimum_required(VERSION 3.4...3.18)` syntax does not work with
+# The `cmake_minimum_required(VERSION 3.4...3.21)` syntax does not work with
 # some versions of VS that have a patched CMake 3.11. This forces us to emulate
 # the behavior using the following workaround:
-if(${CMAKE_VERSION} VERSION_LESS 3.18)
+if(${CMAKE_VERSION} VERSION_LESS 3.21)
   cmake_policy(VERSION ${CMAKE_MAJOR_VERSION}.${CMAKE_MINOR_VERSION})
 else()
-  cmake_policy(VERSION 3.18)
+  cmake_policy(VERSION 3.21)
 endif()
 
 # Extract project version from source
diff --git a/tests/CMakeLists.txt b/tests/CMakeLists.txt
index 374157cfa..873572d60 100644
--- a/tests/CMakeLists.txt
+++ b/tests/CMakeLists.txt
@@ -10,10 +10,10 @@ cmake_minimum_required(VERSION 3.4)
 # The `cmake_minimum_required(VERSION 3.4...3.18)` syntax does not work with
 # some versions of VS that have a patched CMake 3.11. This forces us to emulate
 # the behavior using the following workaround:
-if(${CMAKE_VERSION} VERSION_LESS 3.18)
+if(${CMAKE_VERSION} VERSION_LESS 3.21)
   cmake_policy(VERSION ${CMAKE_MAJOR_VERSION}.${CMAKE_MINOR_VERSION})
 else()
-  cmake_policy(VERSION 3.18)
+  cmake_policy(VERSION 3.21)
 endif()
 
 # Only needed for CMake < 3.5 support
diff --git a/tests/test_cmake_build/installed_embed/CMakeLists.txt b/tests/test_cmake_build/installed_embed/CMakeLists.txt
index 64ae5c4bf..f7d693998 100644
--- a/tests/test_cmake_build/installed_embed/CMakeLists.txt
+++ b/tests/test_cmake_build/installed_embed/CMakeLists.txt
@@ -22,5 +22,7 @@ set_target_properties(test_installed_embed PROPERTIES OUTPUT_NAME test_cmake_bui
 # This may be needed to resolve header conflicts, e.g. between Python release and debug headers.
 set_target_properties(test_installed_embed PROPERTIES NO_SYSTEM_FROM_IMPORTED ON)
 
-add_custom_target(check_installed_embed $<TARGET_FILE:test_installed_embed>
-                                        ${PROJECT_SOURCE_DIR}/../test.py)
+add_custom_target(
+  check_installed_embed
+  $<TARGET_FILE:test_installed_embed> ${PROJECT_SOURCE_DIR}/../test.py
+  DEPENDS test_installed_embed)
diff --git a/tests/test_cmake_build/installed_function/CMakeLists.txt b/tests/test_cmake_build/installed_function/CMakeLists.txt
index 1a502863c..d7ca4db55 100644
--- a/tests/test_cmake_build/installed_function/CMakeLists.txt
+++ b/tests/test_cmake_build/installed_function/CMakeLists.txt
@@ -35,4 +35,5 @@ add_custom_target(
   PYTHONPATH=$<TARGET_FILE_DIR:test_installed_function>
   ${_Python_EXECUTABLE}
   ${PROJECT_SOURCE_DIR}/../test.py
-  ${PROJECT_NAME})
+  ${PROJECT_NAME}
+  DEPENDS test_installed_function)
diff --git a/tests/test_cmake_build/installed_target/CMakeLists.txt b/tests/test_cmake_build/installed_target/CMakeLists.txt
index b38eb7747..bc5e101f1 100644
--- a/tests/test_cmake_build/installed_target/CMakeLists.txt
+++ b/tests/test_cmake_build/installed_target/CMakeLists.txt
@@ -42,4 +42,5 @@ add_custom_target(
   PYTHONPATH=$<TARGET_FILE_DIR:test_installed_target>
   ${_Python_EXECUTABLE}
   ${PROJECT_SOURCE_DIR}/../test.py
-  ${PROJECT_NAME})
+  ${PROJECT_NAME}
+  DEPENDS test_installed_target)
diff --git a/tests/test_cmake_build/subdirectory_embed/CMakeLists.txt b/tests/test_cmake_build/subdirectory_embed/CMakeLists.txt
index dfb9cb8f6..58cdd7cfd 100644
--- a/tests/test_cmake_build/subdirectory_embed/CMakeLists.txt
+++ b/tests/test_cmake_build/subdirectory_embed/CMakeLists.txt
@@ -23,8 +23,10 @@ add_executable(test_subdirectory_embed ../embed.cpp)
 target_link_libraries(test_subdirectory_embed PRIVATE pybind11::embed)
 set_target_properties(test_subdirectory_embed PROPERTIES OUTPUT_NAME test_cmake_build)
 
-add_custom_target(check_subdirectory_embed $<TARGET_FILE:test_subdirectory_embed>
-                                           "${PROJECT_SOURCE_DIR}/../test.py")
+add_custom_target(
+  check_subdirectory_embed
+  $<TARGET_FILE:test_subdirectory_embed> "${PROJECT_SOURCE_DIR}/../test.py"
+  DEPENDS test_subdirectory_embed)
 
 # Test custom export group -- PYBIND11_EXPORT_NAME
 add_library(test_embed_lib ../embed.cpp)
diff --git a/tests/test_cmake_build/subdirectory_function/CMakeLists.txt b/tests/test_cmake_build/subdirectory_function/CMakeLists.txt
index 34aedcf6a..01557c439 100644
--- a/tests/test_cmake_build/subdirectory_function/CMakeLists.txt
+++ b/tests/test_cmake_build/subdirectory_function/CMakeLists.txt
@@ -31,4 +31,5 @@ add_custom_target(
   PYTHONPATH=$<TARGET_FILE_DIR:test_subdirectory_function>
   ${_Python_EXECUTABLE}
   ${PROJECT_SOURCE_DIR}/../test.py
-  ${PROJECT_NAME})
+  ${PROJECT_NAME}
+  DEPENDS test_subdirectory_function)
diff --git a/tests/test_cmake_build/subdirectory_target/CMakeLists.txt b/tests/test_cmake_build/subdirectory_target/CMakeLists.txt
index 31d862f6a..ba82fdee2 100644
--- a/tests/test_cmake_build/subdirectory_target/CMakeLists.txt
+++ b/tests/test_cmake_build/subdirectory_target/CMakeLists.txt
@@ -37,4 +37,5 @@ add_custom_target(
   PYTHONPATH=$<TARGET_FILE_DIR:test_subdirectory_target>
   ${_Python_EXECUTABLE}
   ${PROJECT_SOURCE_DIR}/../test.py
-  ${PROJECT_NAME})
+  ${PROJECT_NAME}
+  DEPENDS test_subdirectory_target)
diff --git a/tests/test_embed/CMakeLists.txt b/tests/test_embed/CMakeLists.txt
index c960c877a..3b89d6e58 100644
--- a/tests/test_embed/CMakeLists.txt
+++ b/tests/test_embed/CMakeLists.txt
@@ -31,6 +31,7 @@ endif()
 add_custom_target(
   cpptest
   COMMAND "$<TARGET_FILE:test_embed>"
+  DEPENDS test_embed
   WORKING_DIRECTORY "${CMAKE_CURRENT_BINARY_DIR}")
 
 pybind11_add_module(external_module THIN_LTO external_module.cpp)