diff --git a/pkgs/build-support/cc-wrapper/default.nix b/pkgs/build-support/cc-wrapper/default.nix
index abc88910c36d2fc..d97f86327c79ad2 100644
--- a/pkgs/build-support/cc-wrapper/default.nix
+++ b/pkgs/build-support/cc-wrapper/default.nix
@@ -331,11 +331,18 @@ stdenv.mkDerivation {
     # compile, because it uses "#include_next <limits.h>" to find the
     # limits.h file in ../includes-fixed. To remedy the problem,
     # another -idirafter is necessary to add that directory again.
+    #
+    # We use --sysroot=/nix/store/does/not/exist to drop embedded default
+    # path to glibc headers gcc was built against. Without it -idirafter
+    # only appends to the list and outdated glibc headers end up being
+    # used. 'cc-cflags-before' is used to allow user's --sysroot= option
+    # to override our default.
     + optionalString (libc != null) (''
       touch "$out/nix-support/libc-cflags"
       touch "$out/nix-support/libc-ldflags"
       echo "-B${libc_lib}${libc.libdir or "/lib/"}" >> $out/nix-support/libc-crt1-cflags
     '' + optionalString (!(cc.langD or false)) ''
+      echo "--sysroot=/nix/store/does/not/exist" >> $out/nix-support/cc-cflags-before
       echo "-idirafter ${libc_dev}${libc.incdir or "/include"}" >> $out/nix-support/libc-cflags
     '' + optionalString (isGNU && (!(cc.langD or false))) ''
       for dir in "${cc}"/lib/gcc/*/*/include-fixed; do
diff --git a/pkgs/stdenv/linux/default.nix b/pkgs/stdenv/linux/default.nix
index 870fb04c3883fee..50c1c5130cf1ab7 100644
--- a/pkgs/stdenv/linux/default.nix
+++ b/pkgs/stdenv/linux/default.nix
@@ -9,14 +9,11 @@
 # is used to build all other packages (including the bootstrapFiles).
 #
 # Goals of the bootstrap process:
-# 1. final stdenv must not reference any of the bootstrap files.
-# 2. final stdenv must not contain any of the bootstrap files
-#    (the only current violation is libgcc_s.so in glibc).
+# 1. final stdenv must not reference any of the bootstrap packages.
+# 2. final stdenv must not contain any of the bootstrap files.
 # 3. final stdenv must not contain any of the files directly
 #    generated by the bootstrap code generators (assembler, linker,
-#    compiler). The only current violations are: libgcc_s.so in glibc,
-#    the lib{mpfr,mpc,gmp,isl} which are statically linked
-#    into the final gcc).
+#    compiler).
 #
 # These goals ensure that final packages and final stdenv are built
 # exclusively using nixpkgs package definitions and don't depend
@@ -109,12 +106,13 @@ let
     '';
 
 
-  # The bootstrap process proceeds in several steps.
-
-
-  # Create a standard environment by downloading pre-built binaries of
-  # coreutils, GCC, etc.
-
+  # The bootstrap process proceeds in several steps. Our high-level plan
+  # is the following:
+  #
+  # - build binutils with bootstrapTools
+  # - build gcc with bootstrapTools
+  # - build glibc with bootstrapTools + gcc from nixpkgs (embed libgcc_s.so.1)
+  # - build gcc with nixpkgs toolchain
 
   # Download and unpack the bootstrap tools (coreutils, GCC, Glibc, ...).
   bootstrapTools = import (if localSystem.libc == "musl" then ./bootstrap-tools-musl else ./bootstrap-tools) {
@@ -284,21 +282,63 @@ in
     };
   })
 
-
   # 2nd stdenv that contains our own rebuilt binutils and is used for
-  # compiling our own Glibc.
+  # compiling our own gcc.
   #
   # resulting stage2 stdenv:
-  # - coreutils, glibc, gcc: from bootstrapFiles
-  # - binutils: from nixpkgs, built by bootstrapFiles toolchain
+  # - coreutils, glibc: from bootstrapFiles
+  # - binutils, gcc: from nixpkgs, built by bootstrapFiles toolchain
   (prevStage: stageFun prevStage {
     name = "bootstrap-stage2";
 
     overrides = self: super: {
       inherit (prevStage)
         ccWrapperStdenv
-        gcc-unwrapped coreutils gnugrep
-        perl gnum4 bison;
+        bash bison gnum4 coreutils gnugrep
+        patchelf perl texinfo xz;
+
+      ${localSystem.libc} = getLibc prevStage;
+
+      gcc-unwrapped =
+        let makeStaticLibrariesAndMark = pkg:
+              lib.makeOverridable (pkg.override { stdenv = self.makeStaticLibraries self.stdenv; })
+                .overrideAttrs (a: { pname = "${a.pname}-stage2"; });
+        in super.gcc-unwrapped.override {
+        # Link GCC statically against GMP etc.  This makes sense because
+        # these builds of the libraries are only used by GCC, so it
+        # reduces the size of the stdenv closure.
+        gmp = makeStaticLibrariesAndMark super.gmp;
+        mpfr = makeStaticLibrariesAndMark super.mpfr;
+        libmpc = makeStaticLibrariesAndMark super.libmpc;
+        isl = makeStaticLibrariesAndMark super.isl_0_20;
+        # Use a deterministically built compiler
+        # see https://github.com/NixOS/nixpkgs/issues/108475 for context
+        reproducibleBuild = true;
+        profiledCompiler = false;
+      };
+    };
+
+    # `libtool` comes with obsolete config.sub/config.guess that don't recognize Risc-V.
+    extraNativeBuildInputs =
+      lib.optional (localSystem.isRiscV) prevStage.updateAutotoolsGnuConfigScriptsHook;
+  })
+
+  # 3rd stdenv that contains our own rebuilt binutils and gcc and is
+  # used for compiling our own Glibc.
+  #
+  # resulting stage3 stdenv:
+  # - coreutils: from bootstrapFiles
+  # - glibc, binutils, gcc: from nixpkgs, built by bootstrapFiles toolchain
+  (prevStage: stageFun prevStage {
+    name = "bootstrap-stage3";
+
+    overrides = self: super: {
+      inherit (prevStage)
+        ccWrapperStdenv
+        gcc-unwrapped
+        bash bison coreutils gnum4 gnugrep
+        patchelf perl;
+
       dejagnu = super.dejagnu.overrideAttrs (a: { doCheck = false; } );
 
       # We need libidn2 and its dependency libunistring as glibc dependency.
@@ -356,21 +396,24 @@ in
   })
 
 
-  # Construct a third stdenv identical to the 2nd, except that this
+  # Construct a fourth stdenv identical to the 3rd, except that this
   # one uses the rebuilt Glibc from stage2.  It still uses the recent
   # binutils and rest of the bootstrap tools, including GCC.
   #
-  # resulting stage3 stdenv:
+  # resulting stage4 stdenv:
   # - coreutils, gcc: from bootstrapFiles
-  # - glibc, binutils: from nixpkgs, built by bootstrapFiles toolchain
+  # - binutils, gcc: from nixpkgs, built by bootstrapFiles toolchain
+  # - glibc: from nixpkgs, built by nixpkgs toolchain
   (prevStage: stageFun prevStage {
-    name = "bootstrap-stage3";
+    name = "bootstrap-stage4";
 
     overrides = self: super: rec {
       inherit (prevStage)
         ccWrapperStdenv
-        binutils coreutils gnugrep
-        perl patchelf linuxHeaders gnum4 bison libidn2 libunistring;
+        bison binutils coreutils gnugrep gnum4
+        patchelf perl texinfo xz
+        linuxHeaders libidn2 libunistring;
+
       ${localSystem.libc} = getLibc prevStage;
       gcc-unwrapped =
         let makeStaticLibrariesAndMark = pkg:
@@ -397,28 +440,27 @@ in
   })
 
 
-  # Construct a fourth stdenv that uses the new GCC.  But coreutils is
+  # Construct a fifth stdenv that uses the new GCC.  But coreutils is
   # still from the bootstrap tools.
   #
-  # resulting stage4 stdenv:
+  # resulting stage5 stdenv:
   # - coreutils: from bootstrapFiles
-  # - glibc, binutils: from nixpkgs, built by bootstrapFiles toolchain
-  # - gcc: from nixpkgs, built by bootstrapFiles toolchain. Can assume
-  #        it has almost no code from bootstrapTools as gcc bootstraps
-  #        internally. The only exceptions are crt files from glibc
-  #        built by bootstrapTools used to link executables and libraries,
-  #        and the bootstrapTools-built, statically-linked
-  #        lib{mpfr,mpc,gmp,isl}.a which are linked into the final gcc
-  #        (see commit cfde88976ba4cddd01b1bb28b40afd12ea93a11d).
+  # - binutils: from nixpkgs, built by bootstrapFiles toolchain
+  # - glibc, gcc: from nixpkgs, built by nixpkgs toolchain
   (prevStage: stageFun prevStage {
-    name = "bootstrap-stage4";
+    name = "bootstrap-stage5";
 
     overrides = self: super: {
       # Zlib has to be inherited and not rebuilt in this stage,
       # because gcc (since JAR support) already depends on zlib, and
       # then if we already have a zlib we want to use that for the
       # other purposes (binutils and top-level pkgs) too.
-      inherit (prevStage) gettext gnum4 bison perl texinfo zlib linuxHeaders libidn2 libunistring;
+      inherit (prevStage)
+          bash gettext gnum4 bison
+          perl texinfo which
+          # xz - rebuild to pull in rebuilt version into final stdenv
+          zlib linuxHeaders libidn2 libunistring;
+
       ${localSystem.libc} = getLibc prevStage;
       binutils = super.binutils.override {
         # Don't use stdenv's shell but our own
@@ -468,15 +510,7 @@ in
   # binutils built.
   #
   # resulting stage5 (final) stdenv:
-  # - coreutils, binutils: from nixpkgs, built by nixpkgs toolchain
-  # - glibc: from nixpkgs, built by bootstrapFiles toolchain
-  # - gcc: from nixpkgs, built by bootstrapFiles toolchain. Can assume
-  #        it has almost no code from bootstrapTools as gcc bootstraps
-  #        internally. The only exceptions are crt files from glibc
-  #        built by bootstrapTools used to link executables and libraries,
-  #        and the bootstrapTools-built, statically-linked
-  #        lib{mpfr,mpc,gmp,isl}.a which are linked into the final gcc
-  #        (see commit cfde88976ba4cddd01b1bb28b40afd12ea93a11d).
+  # - coreutils, binutils, glibc, gcc: from nixpkgs, built by nixpkgs toolchain
   (prevStage: {
     inherit config overlays;
     stdenv = import ../generic rec {