diff --git a/pkgs/stdenv/common-path.nix b/pkgs/stdenv/common-path.nix
index da468d56a2cda..8c1acfb50dd68 100644
--- a/pkgs/stdenv/common-path.nix
+++ b/pkgs/stdenv/common-path.nix
@@ -12,4 +12,12 @@
   pkgs.bash
   pkgs.patch
   pkgs.xz.bin
+
+  # The `file` command is added here because an enormous number of
+  # packages have a vendored dependency upon `file` in their
+  # `./configure` script, due to libtool<=2.4.6, or due to
+  # libtool>=2.4.7 in which the package author decided to set FILECMD
+  # when running libtoolize.  In fact, file-5.4.6 *depends on itself*
+  # and tries to invoke `file` from its own ./configure script.
+  pkgs.file
 ]
diff --git a/pkgs/stdenv/darwin/default.nix b/pkgs/stdenv/darwin/default.nix
index 32e4fe9749ab3..bbc15bad26203 100644
--- a/pkgs/stdenv/darwin/default.nix
+++ b/pkgs/stdenv/darwin/default.nix
@@ -486,6 +486,7 @@ rec {
           gmp
           libiconv
           brotli.lib
+          file
         ] ++ lib.optional haveKRB5 libkrb5) ++
         (with pkgs."${finalLlvmPackages}"; [
           libcxx
@@ -561,6 +562,7 @@ rec {
           gmp
           libiconv
           brotli.lib
+          file
         ] ++ lib.optional haveKRB5 libkrb5) ++
         (with pkgs."${finalLlvmPackages}"; [
           libcxx
@@ -737,6 +739,7 @@ rec {
         brotli.lib
         cc.expand-response-params
         libxml2.out
+        file
       ] ++ lib.optional haveKRB5 libkrb5
       ++ lib.optionals localSystem.isAarch64 [
         pkgs.updateAutotoolsGnuConfigScriptsHook
diff --git a/pkgs/stdenv/generic/setup.sh b/pkgs/stdenv/generic/setup.sh
index 6d30e6c01ffbf..40ffd9344e34d 100644
--- a/pkgs/stdenv/generic/setup.sh
+++ b/pkgs/stdenv/generic/setup.sh
@@ -1021,6 +1021,21 @@ configurePhase() {
             echo "fixing libtool script $i"
             fixLibtool "$i"
         done
+
+        # replace `/usr/bin/file` with `file` in any `configure`
+        # scripts with vendored libtool code.  Preserve mtimes to
+        # prevent some packages (e.g. libidn2) from spontaneously
+        # autoreconf'ing themselves
+        CONFIGURE_MTIME_REFERENCE=$(mktemp configure.mtime.reference.XXX)
+        find . \
+          -executable \
+          -type f \
+          -name configure \
+          -execdir grep -l 'GNU Libtool is free software; you can redistribute it and/or modify' {} \; \
+          -execdir touch -r {} "$CONFIGURE_MTIME_REFERENCE" \; \
+          -execdir sed -i s_/usr/bin/file_file_g {} \;    \
+          -execdir touch -r "$CONFIGURE_MTIME_REFERENCE" {} \;
+        rm -f "$CONFIGURE_MTIME_REFERENCE"
     fi
 
     if [[ -z "${dontAddPrefix:-}" && -n "$prefix" ]]; then
diff --git a/pkgs/stdenv/linux/default.nix b/pkgs/stdenv/linux/default.nix
index 956aeff494623..b00332bae4c9b 100644
--- a/pkgs/stdenv/linux/default.nix
+++ b/pkgs/stdenv/linux/default.nix
@@ -414,7 +414,7 @@ in
         # Simple executable tools
         concatMap (p: [ (getBin p) (getLib p) ]) [
             gzip bzip2 xz bash binutils.bintools coreutils diffutils findutils
-            gawk gnumake gnused gnutar gnugrep gnupatch patchelf ed
+            gawk gnumake gnused gnutar gnugrep gnupatch patchelf ed file
           ]
         # Library dependencies
         ++ map getLib (