diff --git a/include/vcpkg/fwd/vcpkgcmdarguments.h b/include/vcpkg/fwd/vcpkgcmdarguments.h
index f8fbaca821..55d45c3e42 100644
--- a/include/vcpkg/fwd/vcpkgcmdarguments.h
+++ b/include/vcpkg/fwd/vcpkgcmdarguments.h
@@ -11,4 +11,5 @@ namespace vcpkg
     struct HelpTableFormatter;
     struct VcpkgCmdArguments;
     struct FeatureFlagSettings;
+    struct PortApplicableSetting;
 }
diff --git a/include/vcpkg/vcpkgcmdarguments.h b/include/vcpkg/vcpkgcmdarguments.h
index f804051c24..b69d9d7526 100644
--- a/include/vcpkg/vcpkgcmdarguments.h
+++ b/include/vcpkg/vcpkgcmdarguments.h
@@ -80,6 +80,21 @@ namespace vcpkg
         bool dependency_graph;
     };
 
+    struct PortApplicableSetting
+    {
+        std::string value;
+
+        PortApplicableSetting(StringView setting);
+        PortApplicableSetting(const PortApplicableSetting&);
+        PortApplicableSetting(PortApplicableSetting&&);
+        PortApplicableSetting& operator=(const PortApplicableSetting&);
+        PortApplicableSetting& operator=(PortApplicableSetting&&);
+        bool is_port_affected(StringView port_name) const noexcept;
+
+    private:
+        std::vector<std::string> affected_ports;
+    };
+
     struct VcpkgCmdArguments
     {
         static VcpkgCmdArguments create_from_command_line(const ILineReader& fs,
@@ -161,6 +176,11 @@ namespace vcpkg
         constexpr static StringLiteral GITHUB_REPOSITORY_OWNER_ID = "GITHUB_REPOSITORY_OWNER_ID";
         Optional<std::string> github_repository_owner_id;
 
+        constexpr static StringLiteral CMAKE_DEBUGGING_ARG = "cmake-debug";
+        Optional<PortApplicableSetting> cmake_debug;
+        constexpr static StringLiteral CMAKE_CONFIGURE_DEBUGGING_ARG = "cmake-configure-debug";
+        Optional<PortApplicableSetting> cmake_configure_debug;
+
         constexpr static StringLiteral CMAKE_SCRIPT_ARG = "cmake-args";
         std::vector<std::string> cmake_args;
 
diff --git a/src/vcpkg-test/arguments.cpp b/src/vcpkg-test/arguments.cpp
index fa5fd6095f..474eb631f8 100644
--- a/src/vcpkg-test/arguments.cpp
+++ b/src/vcpkg-test/arguments.cpp
@@ -160,3 +160,24 @@ TEST_CASE ("Feature flag off", "[arguments]")
     auto v = VcpkgCmdArguments::create_from_arg_sequence(t.data(), t.data() + t.size());
     CHECK(!v.versions_enabled());
 }
+
+TEST_CASE ("CMake debugger flags", "[arguments]")
+{
+    std::vector<std::string> t = {"--x-cmake-debug",
+                                  "\\\\.\\pipe\\tespipe;zlib;bar;baz",
+                                  "--x-cmake-configure-debug",
+                                  "\\\\.\\pipe\\configure-pipe"};
+    auto v = VcpkgCmdArguments::create_from_arg_sequence(t.data(), t.data() + t.size());
+    auto& cmake_debug = v.cmake_debug.value_or_exit(VCPKG_LINE_INFO);
+    REQUIRE(cmake_debug.value == "\\\\.\\pipe\\tespipe");
+    REQUIRE(!cmake_debug.is_port_affected("7zip"));
+    REQUIRE(cmake_debug.is_port_affected("zlib"));
+    REQUIRE(cmake_debug.is_port_affected("bar"));
+    REQUIRE(cmake_debug.is_port_affected("baz"));
+    REQUIRE(!cmake_debug.is_port_affected("bazz"));
+
+    auto& cmake_configure_debug = v.cmake_configure_debug.value_or_exit(VCPKG_LINE_INFO);
+    REQUIRE(cmake_configure_debug.value == "\\\\.\\pipe\\configure-pipe");
+    REQUIRE(cmake_configure_debug.is_port_affected("7zip"));
+    REQUIRE(cmake_configure_debug.is_port_affected("zlib"));
+}
diff --git a/src/vcpkg/commands.build.cpp b/src/vcpkg/commands.build.cpp
index 0e6c3d8529..a61e03ec60 100644
--- a/src/vcpkg/commands.build.cpp
+++ b/src/vcpkg/commands.build.cpp
@@ -778,6 +778,24 @@ namespace vcpkg
             variables.emplace_back("ARIA2", paths.get_tool_exe(Tools::ARIA2, stdout_sink));
         }
 
+        if (auto cmake_debug = args.cmake_debug.get())
+        {
+            if (cmake_debug->is_port_affected(scf.core_paragraph->name))
+            {
+                variables.emplace_back("--debugger");
+                variables.emplace_back(fmt::format("--debugger-pipe={}", cmake_debug->value));
+            }
+        }
+
+        if (auto cmake_configure_debug = args.cmake_configure_debug.get())
+        {
+            if (cmake_configure_debug->is_port_affected(scf.core_paragraph->name))
+            {
+                variables.emplace_back(fmt::format("-DVCPKG_CMAKE_CONFIGURE_OPTIONS=--debugger;--debugger-pipe={}",
+                                                   cmake_configure_debug->value));
+            }
+        }
+
         for (const auto& cmake_arg : args.cmake_args)
         {
             variables.emplace_back(cmake_arg);
diff --git a/src/vcpkg/vcpkgcmdarguments.cpp b/src/vcpkg/vcpkgcmdarguments.cpp
index 800a8e4f42..595394615e 100644
--- a/src/vcpkg/vcpkgcmdarguments.cpp
+++ b/src/vcpkg/vcpkgcmdarguments.cpp
@@ -10,6 +10,10 @@
 #include <vcpkg/metrics.h>
 #include <vcpkg/vcpkgcmdarguments.h>
 
+#include <algorithm>
+#include <string>
+#include <utility>
+
 namespace
 {
     using namespace vcpkg;
@@ -231,6 +235,28 @@ namespace vcpkg
         }
     }
 
+    PortApplicableSetting::PortApplicableSetting(StringView setting)
+    {
+        auto split = Strings::split(setting, ';');
+        if (!split.empty())
+        {
+            value = std::move(split[0]);
+            split.erase(split.begin());
+            Util::sort(split);
+            affected_ports = std::move(split);
+        }
+    }
+
+    PortApplicableSetting::PortApplicableSetting(const PortApplicableSetting&) = default;
+    PortApplicableSetting::PortApplicableSetting(PortApplicableSetting&&) = default;
+    PortApplicableSetting& PortApplicableSetting::operator=(const PortApplicableSetting&) = default;
+    PortApplicableSetting& PortApplicableSetting::operator=(PortApplicableSetting&&) = default;
+
+    bool PortApplicableSetting::is_port_affected(StringView port_name) const noexcept
+    {
+        return affected_ports.empty() || std::binary_search(affected_ports.begin(), affected_ports.end(), port_name);
+    }
+
     VcpkgCmdArguments VcpkgCmdArguments::create_from_command_line(const ILineReader& fs,
                                                                   const int argc,
                                                                   const CommandLineCharType* const* const argv)
@@ -290,6 +316,18 @@ namespace vcpkg
                                  StabilityTag::Experimental,
                                  args.asset_sources_template_arg,
                                  msg::format(msgAssetSourcesArg));
+        {
+            std::string raw_cmake_debug;
+            if (args.parser.parse_option(CMAKE_DEBUGGING_ARG, StabilityTag::Experimental, raw_cmake_debug))
+            {
+                args.cmake_debug.emplace(raw_cmake_debug);
+            }
+
+            if (args.parser.parse_option(CMAKE_CONFIGURE_DEBUGGING_ARG, StabilityTag::Experimental, raw_cmake_debug))
+            {
+                args.cmake_configure_debug.emplace(raw_cmake_debug);
+            }
+        }
 
         args.parser.parse_multi_option(
             OVERLAY_PORTS_ARG,
@@ -804,5 +842,7 @@ namespace vcpkg
     constexpr StringLiteral VcpkgCmdArguments::VERSIONS_FEATURE;
 
     constexpr StringLiteral VcpkgCmdArguments::CMAKE_SCRIPT_ARG;
+    constexpr StringLiteral VcpkgCmdArguments::CMAKE_DEBUGGING_ARG;
+    constexpr StringLiteral VcpkgCmdArguments::CMAKE_CONFIGURE_DEBUGGING_ARG;
     constexpr StringLiteral VcpkgCmdArguments::EXACT_ABI_TOOLS_VERSIONS_SWITCH;
 }