diff --git a/pkgs/development/interpreters/python/hooks/default.nix b/pkgs/development/interpreters/python/hooks/default.nix
index a653ada4837d4..391ccb463e707 100644
--- a/pkgs/development/interpreters/python/hooks/default.nix
+++ b/pkgs/development/interpreters/python/hooks/default.nix
@@ -1,7 +1,8 @@
 self: dontUse: with self;
 
 let
-  pythonInterpreter = python.pythonForBuild.interpreter;
+  inherit (python) pythonForBuild;
+  pythonInterpreter = pythonForBuild.interpreter;
   pythonSitePackages = python.sitePackages;
   pythonCheckInterpreter = python.interpreter;
   setuppy = ../run_setup.py;
@@ -66,11 +67,9 @@ in {
     makePythonHook {
       name = "pypa-build-hook.sh";
       propagatedBuildInputs = [ build wheel ];
-      substitutions = {
-        inherit pythonInterpreter;
-      };
-    } ./pypa-build-hook.sh) {};
-
+    } ./pypa-build-hook.sh) {
+      inherit (pythonForBuild.pkgs) build;
+    };
 
   pipInstallHook = callPackage ({ makePythonHook, pip }:
     makePythonHook {
@@ -81,6 +80,17 @@ in {
       };
     } ./pip-install-hook.sh) {};
 
+  pypaInstallHook = callPackage ({ makePythonHook, installer }:
+    makePythonHook {
+      name = "pypa-install-hook";
+      propagatedBuildInputs = [ installer ];
+      substitutions = {
+        inherit pythonInterpreter pythonSitePackages;
+      };
+    } ./pypa-install-hook.sh) {
+      inherit (pythonForBuild.pkgs) installer;
+    };
+
   pytestCheckHook = callPackage ({ makePythonHook, pytest }:
     makePythonHook {
       name = "pytest-check-hook";
@@ -133,9 +143,8 @@ in {
   pythonRelaxDepsHook = callPackage ({ makePythonHook, wheel }:
     makePythonHook {
       name = "python-relax-deps-hook";
-      propagatedBuildInputs = [ wheel ];
       substitutions = {
-        inherit pythonInterpreter;
+        inherit pythonInterpreter pythonSitePackages wheel;
       };
     } ./python-relax-deps-hook.sh) {};
 
diff --git a/pkgs/development/interpreters/python/hooks/pypa-build-hook.sh b/pkgs/development/interpreters/python/hooks/pypa-build-hook.sh
index 3b71300497691..5d77613bf565f 100644
--- a/pkgs/development/interpreters/python/hooks/pypa-build-hook.sh
+++ b/pkgs/development/interpreters/python/hooks/pypa-build-hook.sh
@@ -6,7 +6,7 @@ pypaBuildPhase() {
     runHook preBuild
 
     echo "Creating a wheel..."
-    @pythonInterpreter@ -m build --no-isolation --outdir dist/ --wheel $pypaBuildFlags
+    pyproject-build --no-isolation --outdir dist/ --wheel $pypaBuildFlags
     echo "Finished creating a wheel..."
 
     runHook postBuild
diff --git a/pkgs/development/interpreters/python/hooks/pypa-install-hook.sh b/pkgs/development/interpreters/python/hooks/pypa-install-hook.sh
new file mode 100644
index 0000000000000..1a7b30116904a
--- /dev/null
+++ b/pkgs/development/interpreters/python/hooks/pypa-install-hook.sh
@@ -0,0 +1,21 @@
+# Setup hook for PyPA installer.
+echo "Sourcing pypa-install-hook"
+
+pypaInstallPhase() {
+    echo "Executing pypaInstallPhase"
+    runHook preInstall
+
+    for wheel in dist/*.whl; do
+        @pythonInterpreter@ -m installer --prefix "$out" "$wheel"
+    done
+
+    export PYTHONPATH="$out/@pythonSitePackages@:$PYTHONPATH"
+
+    runHook postInstall
+    echo "Finished executing pypaInstallPhase"
+}
+
+if [ -z "${dontUsePypaInstall-}" ] && [ -z "${installPhase-}" ]; then
+    echo "Using pypaInstallPhase"
+    installPhase=pypaInstallPhase
+fi
diff --git a/pkgs/development/interpreters/python/hooks/python-relax-deps-hook.sh b/pkgs/development/interpreters/python/hooks/python-relax-deps-hook.sh
index 31bdec914f690..2c036e90fe54f 100644
--- a/pkgs/development/interpreters/python/hooks/python-relax-deps-hook.sh
+++ b/pkgs/development/interpreters/python/hooks/python-relax-deps-hook.sh
@@ -84,7 +84,8 @@ pythonRelaxDepsHook() {
 
     # We generally shouldn't have multiple wheel files, but let's be safer here
     for wheel in "$pkg_name"*".whl"; do
-        @pythonInterpreter@ -m wheel unpack --dest "$unpack_dir" "$wheel"
+        PYTHONPATH="@wheel@/@pythonSitePackages@:$PYTHONPATH" \
+            @pythonInterpreter@ -m wheel unpack --dest "$unpack_dir" "$wheel"
         rm -rf "$wheel"
 
         _pythonRelaxDeps "$metadata_file"
@@ -95,7 +96,8 @@ pythonRelaxDepsHook() {
             cat "$unpack_dir/$pkg_name/$pkg_name.dist-info/METADATA"
         fi
 
-        @pythonInterpreter@ -m wheel pack "$unpack_dir/$pkg_name"
+        PYTHONPATH="@wheel@/@pythonSitePackages@:$PYTHONPATH" \
+            @pythonInterpreter@ -m wheel pack "$unpack_dir/$pkg_name"
     done
 
     # Remove the folder since it will otherwise be in the dist output.
diff --git a/pkgs/development/interpreters/python/mk-python-derivation.nix b/pkgs/development/interpreters/python/mk-python-derivation.nix
index 79e45b8dc395b..8a75dbf43a742 100644
--- a/pkgs/development/interpreters/python/mk-python-derivation.nix
+++ b/pkgs/development/interpreters/python/mk-python-derivation.nix
@@ -12,8 +12,8 @@
 , update-python-libraries
 , setuptools
 , flitBuildHook
-, pipBuildHook
-, pipInstallHook
+, pypaBuildHook
+, pypaInstallHook
 , pythonCatchConflictsHook
 , pythonImportsCheckHook
 , pythonNamespacesHook
@@ -161,6 +161,20 @@ let
 
     in inputs: builtins.map (checkDrv) inputs;
 
+  isBootstrapInstallPackage = builtins.elem (attrs.pname or null) [
+    "flit-core" "installer"
+  ];
+
+  isBootstrapPackage = isBootstrapInstallPackage || builtins.elem (attrs.pname or null) ([
+    "build" "packaging" "pyproject-hooks" "wheel"
+  ] ++ lib.optionals (python.pythonOlder "3.11") [
+    "tomli"
+  ]);
+
+  isSetuptoolsDependency = builtins.elem (attrs.pname or null) [
+    "setuptools" "wheel"
+  ];
+
   # Keep extra attributes from `attrs`, e.g., `patchPhase', etc.
   self = toPythonModule (stdenv.mkDerivation ((builtins.removeAttrs attrs [
     "disabled" "checkPhase" "checkInputs" "nativeCheckInputs" "doCheck" "doInstallCheck" "dontWrapPythonPrograms" "catchConflicts" "format"
@@ -174,7 +188,15 @@ let
       wrapPython
       ensureNewerSourcesForZipFilesHook  # move to wheel installer (pip) or builder (setuptools, flit, ...)?
       pythonRemoveTestsDirHook
-    ] ++ lib.optionals catchConflicts [
+    ] ++ lib.optionals (catchConflicts && !isBootstrapPackage && !isSetuptoolsDependency) [
+      #
+      # 1. When building a package that is also part of the bootstrap chain, we
+      #    must ignore conflicts after installation, because there will be one with
+      #    the package in the bootstrap.
+      #
+      # 2. When a package is a dependency of setuptools, we must ignore conflicts
+      #    because the hook that checks for conflicts uses setuptools.
+      #
       pythonCatchConflictsHook
     ] ++ lib.optionals removeBinBytecode [
       pythonRemoveBinBytecodeHook
@@ -184,15 +206,26 @@ let
       setuptoolsBuildHook
     ] ++ lib.optionals (format == "flit") [
       flitBuildHook
-    ] ++ lib.optionals (format == "pyproject") [
-      pipBuildHook
-    ] ++ lib.optionals (format == "wheel") [
+    ] ++ lib.optionals (format == "pyproject") [(
+      if isBootstrapPackage then
+        pypaBuildHook.override {
+          inherit (python.pythonForBuild.pkgs.bootstrap) build;
+          wheel = null;
+        }
+      else
+        pypaBuildHook
+    )] ++ lib.optionals (format == "wheel") [
       wheelUnpackHook
     ] ++ lib.optionals (format == "egg") [
       eggUnpackHook eggBuildHook eggInstallHook
-    ] ++ lib.optionals (!(format == "other") || dontUsePipInstall) [
-      pipInstallHook
-    ] ++ lib.optionals (stdenv.buildPlatform == stdenv.hostPlatform) [
+    ] ++ lib.optionals (format != "other") [(
+      if isBootstrapInstallPackage then
+        pypaInstallHook.override {
+          inherit (python.pythonForBuild.pkgs.bootstrap) installer;
+        }
+      else
+        pypaInstallHook
+    )] ++ lib.optionals (stdenv.buildPlatform == stdenv.hostPlatform) [
       # This is a test, however, it should be ran independent of the checkPhase and checkInputs
       pythonImportsCheckHook
     ] ++ lib.optionals (python.pythonAtLeast "3.3") [
diff --git a/pkgs/development/interpreters/python/python-packages-base.nix b/pkgs/development/interpreters/python/python-packages-base.nix
index 6a723413c850c..91ca84b34b83d 100644
--- a/pkgs/development/interpreters/python/python-packages-base.nix
+++ b/pkgs/development/interpreters/python/python-packages-base.nix
@@ -32,12 +32,17 @@ let
       }
       else result;
 
-  buildPythonPackage = makeOverridablePythonPackage (lib.makeOverridable (callPackage ./mk-python-derivation.nix {
+  mkPythonDerivation = if python.isPy3k then
+    ./mk-python-derivation.nix
+  else
+    ./python2/mk-python-derivation.nix;
+
+  buildPythonPackage = makeOverridablePythonPackage (lib.makeOverridable (callPackage mkPythonDerivation {
     inherit namePrefix;     # We want Python libraries to be named like e.g. "python3.6-${name}"
     inherit toPythonModule; # Libraries provide modules
   }));
 
-  buildPythonApplication = makeOverridablePythonPackage (lib.makeOverridable (callPackage ./mk-python-derivation.nix {
+  buildPythonApplication = makeOverridablePythonPackage (lib.makeOverridable (callPackage mkPythonDerivation {
     namePrefix = "";        # Python applications should not have any prefix
     toPythonModule = x: x;  # Application does not provide modules.
   }));
diff --git a/pkgs/development/interpreters/python/python2/mk-python-derivation.nix b/pkgs/development/interpreters/python/python2/mk-python-derivation.nix
new file mode 100644
index 0000000000000..e5f9c00b2fb22
--- /dev/null
+++ b/pkgs/development/interpreters/python/python2/mk-python-derivation.nix
@@ -0,0 +1,252 @@
+# Generic builder only used for EOL and deprecated Python 2.
+
+{ lib
+, config
+, python
+, wrapPython
+, unzip
+, ensureNewerSourcesForZipFilesHook
+# Whether the derivation provides a Python module or not.
+, toPythonModule
+, namePrefix
+, update-python-libraries
+, setuptools
+, pipBuildHook
+, pipInstallHook
+, pythonCatchConflictsHook
+, pythonImportsCheckHook
+, pythonOutputDistHook
+, pythonRemoveBinBytecodeHook
+, pythonRemoveTestsDirHook
+, setuptoolsBuildHook
+, setuptoolsCheckHook
+, wheelUnpackHook
+, eggUnpackHook
+, eggBuildHook
+, eggInstallHook
+}:
+
+{ name ? "${attrs.pname}-${attrs.version}"
+
+# Build-time dependencies for the package
+, nativeBuildInputs ? []
+
+# Run-time dependencies for the package
+, buildInputs ? []
+
+# Dependencies needed for running the checkPhase.
+# These are added to buildInputs when doCheck = true.
+, checkInputs ? []
+, nativeCheckInputs ? []
+
+# propagate build dependencies so in case we have A -> B -> C,
+# C can import package A propagated by B
+, propagatedBuildInputs ? []
+
+# DEPRECATED: use propagatedBuildInputs
+, pythonPath ? []
+
+# Enabled to detect some (native)BuildInputs mistakes
+, strictDeps ? true
+
+, outputs ? [ "out" ]
+
+# used to disable derivation, useful for specific python versions
+, disabled ? false
+
+# Raise an error if two packages are installed with the same name
+# TODO: For cross we probably need a different PYTHONPATH, or not
+# add the runtime deps until after buildPhase.
+, catchConflicts ? (python.stdenv.hostPlatform == python.stdenv.buildPlatform)
+
+# Additional arguments to pass to the makeWrapper function, which wraps
+# generated binaries.
+, makeWrapperArgs ? []
+
+# Skip wrapping of python programs altogether
+, dontWrapPythonPrograms ? false
+
+# Don't use Pip to install a wheel
+# Note this is actually a variable for the pipInstallPhase in pip's setupHook.
+# It's included here to prevent an infinite recursion.
+, dontUsePipInstall ? false
+
+# Skip setting the PYTHONNOUSERSITE environment variable in wrapped programs
+, permitUserSite ? false
+
+# Remove bytecode from bin folder.
+# When a Python script has the extension `.py`, bytecode is generated
+# Typically, executables in bin have no extension, so no bytecode is generated.
+# However, some packages do provide executables with extensions, and thus bytecode is generated.
+, removeBinBytecode ? true
+
+# Several package formats are supported.
+# "setuptools" : Install a common setuptools/distutils based package. This builds a wheel.
+# "wheel" : Install from a pre-compiled wheel.
+# "pyproject": Install a package using a ``pyproject.toml`` file (PEP517). This builds a wheel.
+# "egg": Install a package from an egg.
+# "other" : Provide your own buildPhase and installPhase.
+, format ? "setuptools"
+
+, meta ? {}
+
+, passthru ? {}
+
+, doCheck ? config.doCheckByDefault or false
+
+, disabledTestPaths ? []
+
+, ... } @ attrs:
+
+assert lib.assertMsg (format != "flit") "flit is not a supported Python 2 format";
+
+let
+  inherit (python) stdenv;
+
+  withDistOutput = lib.elem format ["pyproject" "setuptools" "flit" "wheel"];
+
+  name_ = name;
+
+  validatePythonMatches = attrName: let
+    isPythonModule = drv:
+      # all pythonModules have the pythonModule attribute
+      (drv ? "pythonModule")
+      # Some pythonModules are turned in to a pythonApplication by setting the field to false
+      && (!builtins.isBool drv.pythonModule);
+    isMismatchedPython = drv: drv.pythonModule != python;
+
+    optionalLocation = let
+        pos = builtins.unsafeGetAttrPos (if attrs ? "pname" then "pname" else "name") attrs;
+      in lib.optionalString (pos != null) " at ${pos.file}:${toString pos.line}:${toString pos.column}";
+
+    leftPadName = name: against: let
+        len = lib.max (lib.stringLength name) (lib.stringLength against);
+      in lib.strings.fixedWidthString len " " name;
+
+    throwMismatch = drv: let
+      myName = "'${namePrefix}${name}'";
+      theirName = "'${drv.name}'";
+    in throw ''
+      Python version mismatch in ${myName}:
+
+      The Python derivation ${myName} depends on a Python derivation
+      named ${theirName}, but the two derivations use different versions
+      of Python:
+
+          ${leftPadName myName theirName} uses ${python}
+          ${leftPadName theirName myName} uses ${toString drv.pythonModule}
+
+      Possible solutions:
+
+        * If ${theirName} is a Python library, change the reference to ${theirName}
+          in the ${attrName} of ${myName} to use a ${theirName} built from the same
+          version of Python
+
+        * If ${theirName} is used as a tool during the build, move the reference to
+          ${theirName} in ${myName} from ${attrName} to nativeBuildInputs
+
+        * If ${theirName} provides executables that are called at run time, pass its
+          bin path to makeWrapperArgs:
+
+              makeWrapperArgs = [ "--prefix PATH : ''${lib.makeBinPath [ ${lib.getName drv } ] }" ];
+
+      ${optionalLocation}
+    '';
+
+    checkDrv = drv:
+      if (isPythonModule drv) && (isMismatchedPython drv)
+      then throwMismatch drv
+      else drv;
+
+    in inputs: builtins.map (checkDrv) inputs;
+
+  # Keep extra attributes from `attrs`, e.g., `patchPhase', etc.
+  self = toPythonModule (stdenv.mkDerivation ((builtins.removeAttrs attrs [
+    "disabled" "checkPhase" "checkInputs" "nativeCheckInputs" "doCheck" "doInstallCheck" "dontWrapPythonPrograms" "catchConflicts" "format"
+    "disabledTestPaths" "outputs"
+  ]) // {
+
+    name = namePrefix + name_;
+
+    nativeBuildInputs = [
+      python
+      wrapPython
+      ensureNewerSourcesForZipFilesHook  # move to wheel installer (pip) or builder (setuptools, flit, ...)?
+      pythonRemoveTestsDirHook
+    ] ++ lib.optionals catchConflicts [
+      pythonCatchConflictsHook
+    ] ++ lib.optionals removeBinBytecode [
+      pythonRemoveBinBytecodeHook
+    ] ++ lib.optionals (lib.hasSuffix "zip" (attrs.src.name or "")) [
+      unzip
+    ] ++ lib.optionals (format == "setuptools") [
+      setuptoolsBuildHook
+    ] ++ lib.optionals (format == "pyproject") [(
+      pipBuildHook
+    )] ++ lib.optionals (format == "wheel") [
+      wheelUnpackHook
+    ] ++ lib.optionals (format == "egg") [
+      eggUnpackHook eggBuildHook eggInstallHook
+    ] ++ lib.optionals (format != "other") [(
+      pipInstallHook
+    )] ++ lib.optionals (stdenv.buildPlatform == stdenv.hostPlatform) [
+      # This is a test, however, it should be ran independent of the checkPhase and checkInputs
+      pythonImportsCheckHook
+    ] ++ lib.optionals withDistOutput [
+      pythonOutputDistHook
+    ] ++ nativeBuildInputs;
+
+    buildInputs = validatePythonMatches "buildInputs" (buildInputs ++ pythonPath);
+
+    propagatedBuildInputs = validatePythonMatches "propagatedBuildInputs" (propagatedBuildInputs ++ [
+      # we propagate python even for packages transformed with 'toPythonApplication'
+      # this pollutes the PATH but avoids rebuilds
+      # see https://github.com/NixOS/nixpkgs/issues/170887 for more context
+      python
+    ]);
+
+    inherit strictDeps;
+
+    LANG = "${if python.stdenv.isDarwin then "en_US" else "C"}.UTF-8";
+
+    # Python packages don't have a checkPhase, only an installCheckPhase
+    doCheck = false;
+    doInstallCheck = attrs.doCheck or true;
+    nativeInstallCheckInputs = [
+    ] ++ lib.optionals (format == "setuptools") [
+      # Longer-term we should get rid of this and require
+      # users of this function to set the `installCheckPhase` or
+      # pass in a hook that sets it.
+      setuptoolsCheckHook
+    ] ++ nativeCheckInputs;
+    installCheckInputs = checkInputs;
+
+    postFixup = lib.optionalString (!dontWrapPythonPrograms) ''
+      wrapPythonPrograms
+    '' + attrs.postFixup or "";
+
+    # Python packages built through cross-compilation are always for the host platform.
+    disallowedReferences = lib.optionals (python.stdenv.hostPlatform != python.stdenv.buildPlatform) [ python.pythonForBuild ];
+
+    outputs = outputs ++ lib.optional withDistOutput "dist";
+
+    meta = {
+      # default to python's platforms
+      platforms = python.meta.platforms;
+      isBuildPythonPackage = python.meta.platforms;
+    } // meta;
+  } // lib.optionalAttrs (attrs?checkPhase) {
+    # If given use the specified checkPhase, otherwise use the setup hook.
+    # Longer-term we should get rid of `checkPhase` and use `installCheckPhase`.
+    installCheckPhase = attrs.checkPhase;
+  } //  lib.optionalAttrs (disabledTestPaths != []) {
+      disabledTestPaths = lib.escapeShellArgs disabledTestPaths;
+  }));
+
+  passthru.updateScript = let
+      filename = builtins.head (lib.splitString ":" self.meta.position);
+    in attrs.passthru.updateScript or [ update-python-libraries filename ];
+in lib.extendDerivation
+  (disabled -> throw "${name} not supported for interpreter ${python.executable}")
+  passthru
+  self
diff --git a/pkgs/development/python-modules/bootstrap/build/default.nix b/pkgs/development/python-modules/bootstrap/build/default.nix
new file mode 100644
index 0000000000000..639d2e3292cb0
--- /dev/null
+++ b/pkgs/development/python-modules/bootstrap/build/default.nix
@@ -0,0 +1,49 @@
+{ lib
+, stdenv
+, python
+, build
+, flit-core
+, installer
+, packaging
+, pyproject-hooks
+, tomli
+}:
+let
+  buildBootstrapPythonModule = basePackage: attrs: stdenv.mkDerivation ({
+    pname = "${python.libPrefix}-bootstrap-${basePackage.pname}";
+    inherit (basePackage) version src meta;
+
+    buildPhase = ''
+      runHook preBuild
+
+      PYTHONPATH="${flit-core}/${python.sitePackages}" \
+        ${python.interpreter} -m flit_core.wheel
+
+      runHook postBuild
+    '';
+
+    installPhase = ''
+      runHook preInstall
+
+      PYTHONPATH="${installer}/${python.sitePackages}" \
+        ${python.interpreter} -m installer \
+          --destdir "$out" --prefix "" dist/*.whl
+
+      runHook postInstall
+    '';
+  } // attrs);
+
+  bootstrap-packaging = buildBootstrapPythonModule packaging {};
+
+  bootstrap-pyproject-hooks = buildBootstrapPythonModule pyproject-hooks {};
+
+  bootstrap-tomli = buildBootstrapPythonModule tomli {};
+in
+buildBootstrapPythonModule build {
+  propagatedBuildInputs = [
+    bootstrap-packaging
+    bootstrap-pyproject-hooks
+  ] ++ lib.optionals (python.pythonOlder "3.11") [
+    bootstrap-tomli
+  ];
+}
diff --git a/pkgs/development/python-modules/bootstrap/flit-core/default.nix b/pkgs/development/python-modules/bootstrap/flit-core/default.nix
new file mode 100644
index 0000000000000..ab9e52538d341
--- /dev/null
+++ b/pkgs/development/python-modules/bootstrap/flit-core/default.nix
@@ -0,0 +1,29 @@
+{ lib
+, stdenv
+, python
+, flit-core
+}:
+
+stdenv.mkDerivation {
+  pname = "${python.libPrefix}-bootstrap-${flit-core.pname}";
+  inherit (flit-core) version src patches meta;
+
+  sourceRoot = "source/flit_core";
+
+  buildPhase = ''
+    runHook preBuild
+
+    ${python.interpreter} -m flit_core.wheel
+
+    runHook postBuild
+  '';
+
+  installPhase = ''
+    runHook preInstall
+
+    ${python.interpreter} bootstrap_install.py dist/flit_core-*.whl \
+      --install-root "$out" --installdir "/${python.sitePackages}"
+
+    runHook postInstall
+  '';
+}
diff --git a/pkgs/development/python-modules/bootstrap/installer/default.nix b/pkgs/development/python-modules/bootstrap/installer/default.nix
new file mode 100644
index 0000000000000..b569e7fa6dc80
--- /dev/null
+++ b/pkgs/development/python-modules/bootstrap/installer/default.nix
@@ -0,0 +1,29 @@
+{ lib
+, stdenv
+, python
+, flit-core
+, installer
+}:
+
+stdenv.mkDerivation {
+  pname = "${python.libPrefix}-bootstrap-${installer.pname}";
+  inherit (installer) version src meta;
+
+  buildPhase = ''
+    runHook preBuild
+
+    PYTHONPATH="${flit-core}/${python.sitePackages}" \
+      ${python.interpreter} -m flit_core.wheel
+
+    runHook postBuild
+  '';
+
+  installPhase = ''
+    runHook preInstall
+
+    PYTHONPATH=src ${python.interpreter} -m installer \
+      --destdir "$out" --prefix "" dist/installer-*.whl
+
+    runHook postInstall
+  '';
+}
diff --git a/pkgs/development/python-modules/build/default.nix b/pkgs/development/python-modules/build/default.nix
index e7c45afdd317d..a61c6166632b9 100644
--- a/pkgs/development/python-modules/build/default.nix
+++ b/pkgs/development/python-modules/build/default.nix
@@ -1,5 +1,6 @@
 { lib
 , stdenv
+, build
 , buildPythonPackage
 , fetchFromGitHub
 , flit-core
@@ -41,36 +42,52 @@ buildPythonPackage rec {
     tomli
   ];
 
-  nativeCheckInputs = [
-    filelock
-    pytest-mock
-    pytest-rerunfailures
-    pytest-xdist
-    pytestCheckHook
-    setuptools
-    toml
-  ];
+  # We need to disable tests because this package is part of the bootstrap chain
+  # and its test dependencies cannot be built yet when this is being built.
+  doCheck = false;
 
-  pytestFlagsArray = [
-    "-W"
-    "ignore::DeprecationWarning"
-  ];
+  passthru.tests = {
+    pytest = buildPythonPackage {
+      pname = "${pname}-pytest";
+      inherit version;
+      format = "other";
 
-  __darwinAllowLocalNetworking = true;
+      dontBuild = true;
+      dontInstall = true;
 
-  disabledTests = [
-    # Tests often fail with StopIteration
-    "test_isolat"
-    "test_default_pip_is_never_too_old"
-    "test_build"
-    "test_with_get_requires"
-    "test_init"
-    "test_output"
-    "test_wheel_metadata"
-  ] ++ lib.optionals stdenv.isDarwin [
-    # Expects Apple's Python and its quirks
-    "test_can_get_venv_paths_with_conflicting_default_scheme"
-  ];
+      nativeCheckInputs = [
+        build
+        filelock
+        pytest-mock
+        pytest-rerunfailures
+        pytest-xdist
+        pytestCheckHook
+        setuptools
+        toml
+      ];
+
+      pytestFlagsArray = [
+        "-W"
+        "ignore::DeprecationWarning"
+      ];
+
+      __darwinAllowLocalNetworking = true;
+
+      disabledTests = [
+        # Tests often fail with StopIteration
+        "test_isolat"
+        "test_default_pip_is_never_too_old"
+        "test_build"
+        "test_with_get_requires"
+        "test_init"
+        "test_output"
+        "test_wheel_metadata"
+      ] ++ lib.optionals stdenv.isDarwin [
+        # Expects Apple's Python and its quirks
+        "test_can_get_venv_paths_with_conflicting_default_scheme"
+      ];
+    };
+  };
 
   pythonImportsCheck = [
     "build"
diff --git a/pkgs/development/python-modules/cypari2/default.nix b/pkgs/development/python-modules/cypari2/default.nix
index bc8a5df2ed177..70cd89afdcade 100644
--- a/pkgs/development/python-modules/cypari2/default.nix
+++ b/pkgs/development/python-modules/cypari2/default.nix
@@ -37,11 +37,12 @@ buildPythonPackage rec {
     export PYTHONPATH="$out/${python.sitePackages}:$PYTHONPATH"
 
     # install "." instead of "*.whl"
-    ${python.pythonForBuild.pkgs.bootstrapped-pip}/bin/pip install . --no-index --no-warn-script-location --prefix="$out" --no-cache
+    pip install . --no-index --no-warn-script-location --prefix="$out" --no-cache
   '';
 
   nativeBuildInputs = [
     pari
+    python.pythonForBuild.pkgs.pip
   ];
 
   buildInputs = [
diff --git a/pkgs/development/python-modules/installer/default.nix b/pkgs/development/python-modules/installer/default.nix
index 9d3c8185322a1..7bf1f7bff27ac 100644
--- a/pkgs/development/python-modules/installer/default.nix
+++ b/pkgs/development/python-modules/installer/default.nix
@@ -4,6 +4,7 @@
 , fetchFromGitHub
 , pytestCheckHook
 , flit-core
+, installer
 , mock
 }:
 
@@ -21,10 +22,26 @@ buildPythonPackage rec {
 
   nativeBuildInputs = [ flit-core ];
 
-  nativeCheckInputs = [
-    pytestCheckHook
-    mock
-  ];
+  # We need to disable tests because this package is part of the bootstrap chain
+  # and its test dependencies cannot be built yet when this is being built.
+  doCheck = false;
+
+  passthru.tests = {
+    pytest = buildPythonPackage {
+      pname = "${pname}-pytest";
+      inherit version;
+      format = "other";
+
+      dontBuild = true;
+      dontInstall = true;
+
+      nativeCheckInputs = [
+        installer
+        mock
+        pytestCheckHook
+      ];
+    };
+  };
 
   meta = with lib; {
     changelog = "https://github.com/pypa/installer/blob/${src.rev}/docs/changelog.md";
diff --git a/pkgs/development/python-modules/pip-tools/default.nix b/pkgs/development/python-modules/pip-tools/default.nix
index f1fcf59ce2fe1..d549822713556 100644
--- a/pkgs/development/python-modules/pip-tools/default.nix
+++ b/pkgs/development/python-modules/pip-tools/default.nix
@@ -11,19 +11,21 @@
 , pythonOlder
 , setuptools
 , setuptools-scm
+, tomli
+, tomli-w
 , wheel
 }:
 
 buildPythonPackage rec {
   pname = "pip-tools";
-  version = "6.13.0";
+  version = "7.2.0";
   format = "pyproject";
 
-  disabled = pythonOlder "3.7";
+  disabled = pythonOlder "3.8";
 
   src = fetchPypi {
     inherit pname version;
-    hash = "sha256-YdRr0uuAFu1Kkk4Zbm5bCiaM07q9eeWTBIcg2yNSK7E=";
+    hash = "sha256-YWSItTnhS4qoVDbtWXozwpH0iFwdLgvsl0AKvlr/LA0=";
   };
 
   patches = [ ./fix-setup-py-bad-syntax-detection.patch ];
@@ -39,11 +41,16 @@ buildPythonPackage rec {
     pip
     setuptools
     wheel
+  ] ++ lib.optionals (pythonOlder "3.11") [
+    tomli
   ];
 
+  __darwinAllowLocalNetworking = true;
+
   nativeCheckInputs = [
     pytest-xdist
     pytestCheckHook
+    tomli-w
   ];
 
   preCheck = lib.optionalString (stdenv.isDarwin && stdenv.isAarch64) ''
diff --git a/pkgs/development/python-modules/pip/default.nix b/pkgs/development/python-modules/pip/default.nix
index ebac5724d66fa..bc06cb39e247b 100644
--- a/pkgs/development/python-modules/pip/default.nix
+++ b/pkgs/development/python-modules/pip/default.nix
@@ -1,10 +1,12 @@
 { lib
 , buildPythonPackage
-, bootstrapped-pip
 , fetchFromGitHub
+, installShellFiles
 , mock
 , scripttest
+, setuptools
 , virtualenv
+, wheel
 , pretend
 , pytest
 
@@ -14,33 +16,40 @@
 
 buildPythonPackage rec {
   pname = "pip";
-  version = "23.0.1";
-  format = "other";
+  version = "23.2.1";
+  format = "pyproject";
 
   src = fetchFromGitHub {
     owner = "pypa";
     repo = pname;
     rev = "refs/tags/${version}";
-    hash = "sha256-BSonlwKmegrlrQTTIL0avPi61/TY2M0f7kOZpSzPRQk=";
-    name = "${pname}-${version}-source";
+    hash = "sha256-mUlzfYmq1FE3X1/2o7sYJzMgwHRI4ib4EMhpg83VvrI=";
   };
 
-  nativeBuildInputs = [ bootstrapped-pip ];
-
   postPatch = ''
     # Remove vendored Windows PE binaries
     # Note: These are unused but make the package unreproducible.
     find -type f -name '*.exe' -delete
   '';
 
-  # pip detects that we already have bootstrapped_pip "installed", so we need
-  # to force it a little.
-  pipInstallFlags = [ "--ignore-installed" ];
+  nativeBuildInputs = [
+    installShellFiles
+    setuptools
+    wheel
+  ];
 
   nativeCheckInputs = [ mock scripttest virtualenv pretend pytest ];
+
   # Pip wants pytest, but tests are not distributed
   doCheck = false;
 
+  postInstall = ''
+    installShellCompletion --cmd pip \
+      --bash <($out/bin/pip completion --bash) \
+      --fish <($out/bin/pip completion --fish) \
+      --zsh <($out/bin/pip completion --zsh)
+  '';
+
   passthru.tests = { inherit pip-tools; };
 
   meta = {
@@ -48,6 +57,5 @@ buildPythonPackage rec {
     license = with lib.licenses; [ mit ];
     homepage = "https://pip.pypa.io/";
     changelog = "https://pip.pypa.io/en/stable/news/#v${lib.replaceStrings [ "." ] [ "-" ] version}";
-    priority = 10;
   };
 }
diff --git a/pkgs/development/python-modules/pyproject-api/default.nix b/pkgs/development/python-modules/pyproject-api/default.nix
index 6ca6ac25a98d3..6cbef5b8a77f1 100644
--- a/pkgs/development/python-modules/pyproject-api/default.nix
+++ b/pkgs/development/python-modules/pyproject-api/default.nix
@@ -6,7 +6,6 @@
 # build time
 , hatchling
 , hatch-vcs
-, setuptools-scm
 
 # runtime
 , packaging
@@ -21,13 +20,14 @@
 # tests
 , pytest-mock
 , pytestCheckHook
+, setuptools
 , virtualenv
 , wheel
 }:
 
 buildPythonPackage rec {
   pname = "pyproject-api";
-  version = "1.5.0";
+  version = "1.5.4";
   format = "pyproject";
 
   disabled = pythonOlder "3.8";
@@ -36,7 +36,7 @@ buildPythonPackage rec {
     owner = "tox-dev";
     repo = "pyproject-api";
     rev = "refs/tags/${version}";
-    hash = "sha256-VO+huA9i7uMpCVaWHC29XlfestSu+N9vWWHteY21uqs=";
+    hash = "sha256-HX+5BypfEOfQ3vg3vha0QCVrEarjMu/Q8id+xgmWGfA=";
   };
 
   outputs = [
@@ -44,12 +44,11 @@ buildPythonPackage rec {
     "doc"
   ];
 
-  SETUPTOOLS_SCM_PRETEND_VERSION = version;
+  env.SETUPTOOLS_SCM_PRETEND_VERSION = version;
 
   nativeBuildInputs = [
     hatchling
     hatch-vcs
-    setuptools-scm
 
     # docs
     sphinxHook
@@ -66,6 +65,7 @@ buildPythonPackage rec {
   nativeCheckInputs = [
     pytest-mock
     pytestCheckHook
+    setuptools
     virtualenv
     wheel
   ];
diff --git a/pkgs/development/python-modules/pyproject-hooks/default.nix b/pkgs/development/python-modules/pyproject-hooks/default.nix
index 76bf3902c3d21..147e173db2daa 100644
--- a/pkgs/development/python-modules/pyproject-hooks/default.nix
+++ b/pkgs/development/python-modules/pyproject-hooks/default.nix
@@ -2,6 +2,7 @@
 , buildPythonPackage
 , fetchPypi
 , flit-core
+, pyproject-hooks
 , pytestCheckHook
 , pythonOlder
 , setuptools
@@ -31,17 +32,33 @@ buildPythonPackage rec {
     tomli
   ];
 
-  nativeCheckInputs = [
-    pytestCheckHook
-    setuptools
-    testpath
-  ];
+  # We need to disable tests because this package is part of the bootstrap chain
+  # and its test dependencies cannot be built yet when this is being built.
+  doCheck = false;
 
-  disabledTests = [
-    # fail to import setuptools
-    "test_setup_py"
-    "test_issue_104"
-  ];
+  passthru.tests = {
+    pytest = buildPythonPackage {
+      pname = "${pname}-pytest";
+      inherit version;
+      format = "other";
+
+      dontBuild = true;
+      dontInstall = true;
+
+      nativeCheckInputs = [
+        pyproject-hooks
+        pytestCheckHook
+        setuptools
+        testpath
+      ];
+
+      disabledTests = [
+        # fail to import setuptools
+        "test_setup_py"
+        "test_issue_104"
+      ];
+    };
+  };
 
   pythonImportsCheck = [
     "pyproject_hooks"
diff --git a/pkgs/development/python-modules/setuptools/default.nix b/pkgs/development/python-modules/setuptools/default.nix
index c851cef24b308..ad7638f3cb38b 100644
--- a/pkgs/development/python-modules/setuptools/default.nix
+++ b/pkgs/development/python-modules/setuptools/default.nix
@@ -1,73 +1,36 @@
 { stdenv
+, lib
 , buildPythonPackage
 , fetchFromGitHub
 , python
-, bootstrapped-pip
-, lib
-, pipInstallHook
-, setuptoolsBuildHook
+, wheel
 }:
 
-let
+buildPythonPackage rec {
   pname = "setuptools";
-  version = "67.4.0";
-
-  # Create an sdist of setuptools
-  sdist = stdenv.mkDerivation rec {
-    name = "${pname}-${version}-sdist.tar.gz";
-
-    src = fetchFromGitHub {
-      owner = "pypa";
-      repo = pname;
-      rev = "refs/tags/v${version}";
-      hash = "sha256-QDHycUFA2VRUE9alan8rF0efZTNV3Jt0CskjkCc+in0=";
-      name = "${pname}-${version}-source";
-    };
-
-    patches = [
-      ./tag-date.patch
-      ./setuptools-distutils-C++.patch
-    ];
-
-    buildPhase = ''
-      ${python.pythonForBuild.interpreter} setup.py egg_info
-      ${python.pythonForBuild.interpreter} setup.py sdist --formats=gztar
-
-      # Here we untar the sdist and retar it in order to control the timestamps
-      # of all the files included
-      tar -xzf dist/${pname}-${version}.post0.tar.gz -C dist/
-      tar -czf dist/${name} -C dist/ --mtime="@$SOURCE_DATE_EPOCH" --sort=name ${pname}-${version}.post0
-    '';
-
-    installPhase = ''
-      echo "Moving sdist..."
-      mv dist/${name} $out
-    '';
+  version = "68.0.0";
+  format = "pyproject";
+
+  src = fetchFromGitHub {
+    owner = "pypa";
+    repo = "setuptools";
+    rev = "refs/tags/v${version}";
+    hash = "sha256-Ew/DpI5XsYMB4kBfkFeeB5wv5cjx4oYTddZCWLgBHBs=";
   };
-in buildPythonPackage {
-  inherit pname version;
-  # Because of bootstrapping we don't use the setuptoolsBuildHook that comes with format="setuptools" directly.
-  # Instead, we override it to remove setuptools to avoid a circular dependency.
-  # The same is done for pip and the pipInstallHook.
-  format = "other";
 
-  src = sdist;
+  patches = [
+    ./tag-date.patch
+    ./setuptools-distutils-C++.patch
+  ];
 
   nativeBuildInputs = [
-    bootstrapped-pip
-    (pipInstallHook.override{pip=null;})
-    (setuptoolsBuildHook.override{setuptools=null; wheel=null;})
+    wheel
   ];
 
   preBuild = lib.optionalString (!stdenv.hostPlatform.isWindows) ''
     export SETUPTOOLS_INSTALL_WINDOWS_SPECIFIC_FILES=0
   '';
 
-  pipInstallFlags = [ "--ignore-installed" ];
-
-  # Adds setuptools to nativeBuildInputs causing infinite recursion.
-  catchConflicts = false;
-
   # Requires pytest, causing infinite recursion.
   doCheck = false;
 
@@ -77,7 +40,6 @@ in buildPythonPackage {
     changelog = "https://setuptools.pypa.io/en/stable/history.html#v${replaceStrings [ "." ] [ "-" ] version}";
     license = with licenses; [ mit ];
     platforms = python.meta.platforms;
-    priority = 10;
     maintainers = teams.python.members;
   };
 }
diff --git a/pkgs/development/python-modules/wheel/default.nix b/pkgs/development/python-modules/wheel/default.nix
index 3be508a0ec590..16c6c2dc087d1 100644
--- a/pkgs/development/python-modules/wheel/default.nix
+++ b/pkgs/development/python-modules/wheel/default.nix
@@ -1,21 +1,19 @@
 { lib
 , buildPythonPackage
 , fetchFromGitHub
-, bootstrapped-pip
-, setuptools
+, flit-core
 }:
 
 buildPythonPackage rec {
   pname = "wheel";
-  version = "0.38.4";
-  format = "other";
+  version = "0.41.1";
+  format = "pyproject";
 
   src = fetchFromGitHub {
     owner = "pypa";
     repo = pname;
     rev = version;
-    hash = "sha256-yZLU0t/nz6kfnnoLL15bybOxN4+SJUaTJsCpGffl1QU=";
-    name = "${pname}-${version}-source";
+    hash = "sha256-/EaDJ2zI/ly2BrrGhiZGwiBYDVPYWTki+87UqtCS3bw=";
     postFetch = ''
       cd $out
       mv tests/testdata/unicode.dist/unicodedist/åäö_日本語.py \
@@ -25,16 +23,13 @@ buildPythonPackage rec {
   };
 
   nativeBuildInputs = [
-    bootstrapped-pip
-    setuptools
+    flit-core
   ];
 
   # No tests in archive
   doCheck = false;
-  pythonImportsCheck = [ "wheel" ];
 
-  # We add this flag to ignore the copy installed by bootstrapped-pip
-  pipInstallFlags = [ "--ignore-installed" ];
+  pythonImportsCheck = [ "wheel" ];
 
   meta = with lib; {
     homepage = "https://github.com/pypa/wheel";
diff --git a/pkgs/development/tools/poetry2nix/poetry2nix/overrides/build-systems.json b/pkgs/development/tools/poetry2nix/poetry2nix/overrides/build-systems.json
index b212fffc1b1c6..176881caeed1f 100644
--- a/pkgs/development/tools/poetry2nix/poetry2nix/overrides/build-systems.json
+++ b/pkgs/development/tools/poetry2nix/poetry2nix/overrides/build-systems.json
@@ -2505,8 +2505,14 @@
     "setuptools"
   ],
   "build": [
-    "flit-core",
-    "setuptools"
+    {
+      "buildSystem": "setuptools",
+      "until": "0.10.0"
+    },
+    {
+      "buildSystem": "flit-core",
+      "from": "0.10.0"
+    }
   ],
   "buildbot": [
     "setuptools"
@@ -5812,11 +5818,7 @@
     "setuptools"
   ],
   "flit": [
-    "flit-core",
-    "setuptools"
-  ],
-  "flit-core": [
-    "setuptools"
+    "flit-core"
   ],
   "flit-scm": [
     "flit-core",
@@ -7540,8 +7542,7 @@
     "setuptools"
   ],
   "installer": [
-    "flit-core",
-    "setuptools"
+    "flit-core"
   ],
   "insteon-frontend-home-assistant": [
     "setuptools"
@@ -10863,8 +10864,24 @@
     "setuptools"
   ],
   "packaging": [
-    "flit-core",
-    "setuptools"
+    {
+      "buildSystem": "setuptools",
+      "until": "20.4"
+    },
+    {
+      "buildSystem": "flit-core",
+      "from": "20.4",
+      "until": "20.8"
+    },
+    {
+      "buildSystem": "setuptools",
+      "from": "20.8",
+      "until": "22.0"
+    },
+    {
+      "buildSystem": "flit-core",
+      "from": "22.0"
+    }
   ],
   "packbits": [
     "setuptools"
@@ -18088,8 +18105,14 @@
     "poetry"
   ],
   "tomli": [
-    "flit-core",
-    "setuptools"
+    {
+      "buildSystem": "poetry-core",
+      "until": "1.0.2"
+    },
+    {
+      "buildSystem": "flit-core",
+      "from": "1.0.2"
+    }
   ],
   "tomli-w": [
     "flit-core",
@@ -19331,7 +19354,14 @@
     "setuptools"
   ],
   "wheel": [
-    "setuptools"
+    {
+      "buildSystem": "setuptools",
+      "until": "0.40.0"
+    },
+    {
+      "buildSystem": "flit-core",
+      "from": "0.40.0"
+    }
   ],
   "wheel-filename": [
     "setuptools"
diff --git a/pkgs/development/tools/poetry2nix/poetry2nix/overrides/default.nix b/pkgs/development/tools/poetry2nix/poetry2nix/overrides/default.nix
index 14338423ec390..d96d920c70940 100644
--- a/pkgs/development/tools/poetry2nix/poetry2nix/overrides/default.nix
+++ b/pkgs/development/tools/poetry2nix/poetry2nix/overrides/default.nix
@@ -2738,15 +2738,12 @@ lib.composeManyExtensions [
         }
       );
 
-      wheel = ((
-        pkgs.python3.pkgs.override {
-          python = self.python;
+      wheel = if self.python.isPy2 then
+        super.wheel.override {
+          inherit (self) bootstrapped-pip;
         }
-      ).wheel.override {
-        inherit (self) buildPythonPackage bootstrapped-pip setuptools;
-      }).overrideAttrs (old: {
-        inherit (super.wheel) pname name version src;
-      });
+      else
+        super.wheel;
 
       zipp = if super.zipp == null then null else
       super.zipp.overridePythonAttrs (
@@ -2757,20 +2754,6 @@ lib.composeManyExtensions [
         }
       );
 
-      packaging =
-        let
-          old = super.packaging;
-        in
-        # From 20.5 until 20.7, packaging used flit for packaging (heh)
-          # See https://github.com/pypa/packaging/pull/352 and https://github.com/pypa/packaging/pull/367
-        if (lib.versionAtLeast old.version "20.5" && lib.versionOlder old.version "20.8") then
-          addBuildSystem
-            {
-              inherit self;
-              drv = old;
-              attr = "flit-core";
-            } else old;
-
       psutil = super.psutil.overridePythonAttrs (
         old: {
           buildInputs = (old.buildInputs or [ ]) ++
diff --git a/pkgs/top-level/python-packages.nix b/pkgs/top-level/python-packages.nix
index 4f52bf39033c8..aa05eb038f6c9 100644
--- a/pkgs/top-level/python-packages.nix
+++ b/pkgs/top-level/python-packages.nix
@@ -8,6 +8,16 @@
 
 self: super: with self; {
 
+  bootstrap = lib.recurseIntoAttrs {
+    flit-core = toPythonModule (callPackage ../development/python-modules/bootstrap/flit-core { });
+    installer = toPythonModule (callPackage ../development/python-modules/bootstrap/installer {
+      inherit (bootstrap) flit-core;
+    });
+    build = toPythonModule (callPackage ../development/python-modules/bootstrap/build {
+      inherit (bootstrap) flit-core installer;
+    });
+  };
+
   bootstrapped-pip = toPythonModule (callPackage ../development/python-modules/bootstrapped-pip { });
 
   setuptools = callPackage ../development/python-modules/setuptools { };