diff --git a/news/4025.fixed.md b/news/4025.fixed.md
new file mode 100644
index 0000000000..80e81333f6
--- /dev/null
+++ b/news/4025.fixed.md
@@ -0,0 +1,3 @@
+(pypi) Fixed {obj}`RECORD` file paths for extracted `.data` directory contents
+so that {obj}`importlib.metadata.files()` correctly locates installed
+distribution files ([#4025](https://github.com/bazel-contrib/rules_python/pull/4025)).
diff --git a/python/private/pypi/BUILD.bazel b/python/private/pypi/BUILD.bazel
index bb84ff9280..7b8349e174 100644
--- a/python/private/pypi/BUILD.bazel
+++ b/python/private/pypi/BUILD.bazel
@@ -41,6 +41,15 @@ alias(
     visibility = ["//visibility:public"],
 )
 
+alias(
+    name = "wheel_record_rewriter",
+    actual = select({
+        "@platforms//os:windows": "wheel_record_rewriter.ps1",
+        "//conditions:default": "wheel_record_rewriter.sh",
+    }),
+    visibility = ["//visibility:public"],
+)
+
 exports_files(
     srcs = ["deps.bzl"],
     visibility = ["//tools/private/update_deps:__pkg__"],
@@ -490,11 +499,20 @@ bzl_library(
     ],
 )
 
+bzl_library(
+    name = "gen_wheel_record",
+    srcs = ["gen_wheel_record.bzl"],
+    deps = [
+        "//python/private:common",
+    ],
+)
+
 bzl_library(
     name = "whl_library_targets",
     srcs = ["whl_library_targets.bzl"],
     deps = [
         ":env_marker_setting",
+        ":gen_wheel_record",
         ":labels",
         ":namespace_pkgs",
         ":pep508_deps",
diff --git a/python/private/pypi/gen_wheel_record.bzl b/python/private/pypi/gen_wheel_record.bzl
new file mode 100644
index 0000000000..e709614b91
--- /dev/null
+++ b/python/private/pypi/gen_wheel_record.bzl
@@ -0,0 +1,83 @@
+"""Rule for generating platform-specific RECORD files."""
+
+load("//python/private:common.bzl", "is_windows_platform")
+
+def _gen_wheel_record_impl(ctx):
+    is_windows = is_windows_platform(ctx)
+    rewriter_file = ctx.files._wheel_record_rewriter[0]
+    out_files = []
+
+    for in_file in ctx.files.srcs:
+        dist_info_name = in_file.dirname.rpartition("/")[2]
+        if dist_info_name:
+            if dist_info_name.endswith(".dist-info"):
+                data_dir_basename = (
+                    dist_info_name[:-len(".dist-info")] + ".data"
+                )
+            else:
+                data_dir_basename = dist_info_name + ".data"
+            out_file = ctx.actions.declare_file(
+                "site-packages/{}/RECORD".format(dist_info_name),
+            )
+        else:
+            data_dir_basename = "data"
+            out_file = ctx.actions.declare_file("site-packages/RECORD")
+
+        out_files.append(out_file)
+
+        action_args = ctx.actions.args()
+        inputs = depset([in_file, rewriter_file])
+
+        if rewriter_file.path.endswith(".ps1"):
+            action_exe = "powershell.exe"
+            action_args.add_all([
+                "-ExecutionPolicy",
+                "Bypass",
+                "-NoProfile",
+                "-File",
+                rewriter_file,
+            ])
+        else:
+            action_exe = (
+                ctx.attr._wheel_record_rewriter[DefaultInfo].files_to_run
+            )
+
+        action_args.add(in_file)
+        action_args.add(out_file)
+        action_args.add("windows" if is_windows else "unix")
+        action_args.add(data_dir_basename)
+
+        ctx.actions.run(
+            inputs = inputs,
+            outputs = [out_file],
+            executable = action_exe,
+            arguments = [action_args],
+            mnemonic = "PyGenWheelRecord",
+            progress_message = "Generating wheel RECORD %{output}",
+            toolchain = None,
+        )
+
+    return [
+        DefaultInfo(files = depset(out_files)),
+    ]
+
+gen_wheel_record = rule(
+    implementation = _gen_wheel_record_impl,
+    attrs = {
+        "srcs": attr.label_list(
+            doc = "The original RECORD files to rewrite.",
+            mandatory = True,
+            allow_files = True,
+        ),
+        "_wheel_record_rewriter": attr.label(
+            default = "//python/private/pypi:wheel_record_rewriter",
+            allow_files = True,
+            cfg = "exec",
+        ),
+        "_windows_constraints": attr.label_list(
+            default = [
+                "@platforms//os:windows",
+            ],
+        ),
+    },
+)
diff --git a/python/private/pypi/wheel_record_rewriter.ps1 b/python/private/pypi/wheel_record_rewriter.ps1
new file mode 100644
index 0000000000..60dd0eca11
--- /dev/null
+++ b/python/private/pypi/wheel_record_rewriter.ps1
@@ -0,0 +1,66 @@
+[CmdletBinding()]
+param(
+    [Parameter(Position=0, Mandatory=$true)]
+    [string]$InFile,
+
+    [Parameter(Position=1, Mandatory=$true)]
+    [string]$OutFile,
+
+    [Parameter(Position=2, Mandatory=$true)]
+    [string]$TargetOs,
+
+    [Parameter(Position=3, Mandatory=$true)]
+    [string]$DataDirBasename
+)
+
+$ErrorActionPreference = "Stop"
+
+$dataPrefix = "$DataDirBasename/"
+$quotedDataPrefix = "`"$DataDirBasename/"
+
+if ($TargetOs -eq "windows") {
+    $dataRepl = "../../"
+    $headersRepl = "../../Include/"
+    $platlibRepl = ""
+    $purelibRepl = ""
+    $scriptsRepl = "../../Scripts/"
+} else {
+    $dataRepl = "../../../"
+    $headersRepl = "../../../include/"
+    $platlibRepl = ""
+    $purelibRepl = ""
+    $scriptsRepl = "../../../bin/"
+}
+
+$lines = Get-Content -Path $InFile
+$outLines = [System.Collections.Generic.List[string]]::new()
+$Utf8NoBom = New-Object System.Text.UTF8Encoding $False
+
+foreach ($line in $lines) {
+    if ($line.StartsWith($quotedDataPrefix)) {
+        $quote = "`""
+        $rest = $line.Substring($quotedDataPrefix.Length)
+    } elseif ($line.StartsWith($dataPrefix)) {
+        $quote = ""
+        $rest = $line.Substring($dataPrefix.Length)
+    } else {
+        $outLines.Add($line)
+        continue
+    }
+
+    if ($rest.StartsWith("purelib/")) {
+        $outLines.Add($quote + $purelibRepl + $rest.Substring(8))
+    } elseif ($rest.StartsWith("platlib/")) {
+        $outLines.Add($quote + $platlibRepl + $rest.Substring(8))
+    } elseif ($rest.StartsWith("scripts/")) {
+        $outLines.Add($quote + $scriptsRepl + $rest.Substring(8))
+    } elseif ($rest.StartsWith("headers/")) {
+        $outLines.Add($quote + $headersRepl + $rest.Substring(8))
+    } elseif ($rest.StartsWith("data/")) {
+        $outLines.Add($quote + $dataRepl + $rest.Substring(5))
+    } else {
+        $outLines.Add($line)
+    }
+}
+
+[System.IO.File]::WriteAllText($OutFile, ($outLines -join "`n") + "`n", $Utf8NoBom)
diff --git a/python/private/pypi/wheel_record_rewriter.sh b/python/private/pypi/wheel_record_rewriter.sh
new file mode 100755
index 0000000000..10189435e1
--- /dev/null
+++ b/python/private/pypi/wheel_record_rewriter.sh
@@ -0,0 +1,60 @@
+#!/bin/sh
+set -eu
+
+IN="$1"
+OUT="$2"
+TARGET_OS="$3"
+DATA_DIR_BASENAME="$4"
+
+DATA_PREFIX="${DATA_DIR_BASENAME}/"
+QUOTED_DATA_PREFIX="\"${DATA_DIR_BASENAME}/"
+
+if [ "$TARGET_OS" = "windows" ]; then
+  DATA_REPL="../../"
+  HEADERS_REPL="../../Include/"
+  PLATLIB_REPL=""
+  PURELIB_REPL=""
+  SCRIPTS_REPL="../../Scripts/"
+else
+  DATA_REPL="../../../"
+  HEADERS_REPL="../../../include/"
+  PLATLIB_REPL=""
+  PURELIB_REPL=""
+  SCRIPTS_REPL="../../../bin/"
+fi
+
+awk -v data_prefix="$DATA_PREFIX" \
+    -v quoted_data_prefix="$QUOTED_DATA_PREFIX" \
+    -v data_repl="$DATA_REPL" \
+    -v headers_repl="$HEADERS_REPL" \
+    -v platlib_repl="$PLATLIB_REPL" \
+    -v purelib_repl="$PURELIB_REPL" \
+    -v scripts_repl="$SCRIPTS_REPL" '
+{
+  line = $0
+  quote = ""
+  if (substr(line, 1, length(quoted_data_prefix)) == quoted_data_prefix) {
+    quote = "\""
+    rest = substr(line, length(quoted_data_prefix) + 1)
+  } else if (substr(line, 1, length(data_prefix)) == data_prefix) {
+    rest = substr(line, length(data_prefix) + 1)
+  } else {
+    print line
+    next
+  }
+
+  if (substr(rest, 1, 8) == "purelib/") {
+    print quote purelib_repl substr(rest, 9)
+  } else if (substr(rest, 1, 8) == "platlib/") {
+    print quote platlib_repl substr(rest, 9)
+  } else if (substr(rest, 1, 8) == "scripts/") {
+    print quote scripts_repl substr(rest, 9)
+  } else if (substr(rest, 1, 8) == "headers/") {
+    print quote headers_repl substr(rest, 9)
+  } else if (substr(rest, 1, 5) == "data/") {
+    print quote data_repl substr(rest, 6)
+  } else {
+    print line
+  }
+}
+' "$IN" > "$OUT"
diff --git a/python/private/pypi/whl_extract.bzl b/python/private/pypi/whl_extract.bzl
index 0d61b9a07b..5dd6d218f8 100644
--- a/python/private/pypi/whl_extract.bzl
+++ b/python/private/pypi/whl_extract.bzl
@@ -36,20 +36,7 @@ def whl_extract(rctx, *, whl_path, logger):
     # Get the <prefix>.dist_info dir name
     data_dir = dist_info_dir.dirname.get_child(dist_info_dir.basename[:-len(".dist-info")] + ".data")
     if data_dir.exists:
-        for prefix, dest_prefix in {
-            # https://docs.python.org/3/library/sysconfig.html#posix-prefix
-            # We are taking this from the legacy whl installer config
-            "data": "data",
-            "headers": "include",
-            # In theory there may be directory collisions here, so it would be best to
-            # merge the paths here. We are doing for quite a few levels deep. What is
-            # more, this code has to be reasonably efficient because some packages like
-            # to not put everything to the top level, but to indicate explicitly if
-            # something is in `platlib` or `purelib` (e.g. libclang wheel).
-            "platlib": "site-packages",
-            "purelib": "site-packages",
-            "scripts": "bin",
-        }.items():
+        for prefix, dest_prefix in _DATA_CATEGORIES.items():
             src = data_dir.get_child(prefix)
             if not src.exists:
                 # The prefix does not exist in the wheel, we can continue
@@ -61,9 +48,32 @@ def whl_extract(rctx, *, whl_path, logger):
                 logger.debug(lambda: "Renaming: {} -> {}".format(src, dest))
                 repo_utils.rename(rctx, src, dest)
 
+        # Move RECORD to rewrite-record so gen_wheel_record can generate
+        # the platform-specific RECORD file at build time.
+        record_file = dist_info_dir.get_child("RECORD")
+        if record_file.exists:
+            rewrite_record_dir = rctx.path("rewrite-record/" + dist_info_dir.basename)
+            repo_utils.mkdir(rctx, rewrite_record_dir)
+            repo_utils.rename(rctx, record_file, rewrite_record_dir.get_child("RECORD"))
+
         # Ensure that there is no data dir left
         rctx.delete(data_dir)
 
+# Mapping of wheel .data categories to their extraction destination (relative to
+# repository root).
+_DATA_CATEGORIES = {
+    # category: repo_dest_dir
+    "data": "data",
+    "headers": "include",
+    # In theory there may be directory collisions in platlib/purelib, so it is
+    # best to merge the paths here. What is more, this code has to be reasonably
+    # efficient because some packages like to explicitly indicate if something
+    # is in `platlib` or `purelib` (e.g. libclang wheel).
+    "platlib": "site-packages",
+    "purelib": "site-packages",
+    "scripts": "bin",
+}
+
 def merge_trees(src, dest):
     """Merge src into the destination path.
 
diff --git a/python/private/pypi/whl_library_targets.bzl b/python/private/pypi/whl_library_targets.bzl
index ee5c781b3d..b7fdbd55e9 100644
--- a/python/private/pypi/whl_library_targets.bzl
+++ b/python/private/pypi/whl_library_targets.bzl
@@ -19,6 +19,7 @@ load("//python:py_binary.bzl", "py_binary")
 load("//python:py_library.bzl", "py_library")
 load("//python/private:normalize_name.bzl", "normalize_name")
 load(":env_marker_setting.bzl", "env_marker_setting")
+load(":gen_wheel_record.bzl", "gen_wheel_record")
 load(
     ":labels.bzl",
     "DATA_LABEL",
@@ -159,6 +160,7 @@ def whl_library_srcs(
             py_library = py_library,
             venv_entry_point = venv_entry_point,
             venv_rewrite_shebang = venv_rewrite_shebang,
+            gen_wheel_record = gen_wheel_record,
             env_marker_setting = env_marker_setting,
             create_inits = _create_inits,
         )):
@@ -225,6 +227,16 @@ def whl_library_srcs(
         bins_for_data_label.append(rewrite_target_name)
         data.append(rewrite_target_name)
 
+    record_srcs = native.glob(["rewrite-record/*/RECORD"], allow_empty = True)
+    record_target_name = "record"
+    if record_srcs:
+        rules.gen_wheel_record(
+            name = record_target_name,
+            srcs = record_srcs,
+            tags = ["manual"],
+        )
+        data.append(record_target_name)
+
     if filegroups == None:
         filegroups = {
             EXTRACTED_WHEEL_FILES: dict(
@@ -248,6 +260,8 @@ def whl_library_srcs(
         srcs = native.glob(**glob_kwargs)
         if filegroup_name == DATA_LABEL:
             srcs = srcs + bins_for_data_label
+        if filegroup_name == DIST_INFO_LABEL and record_srcs:
+            srcs = srcs + [record_target_name]
         native.filegroup(
             name = filegroup_name,
             srcs = srcs,
diff --git a/tests/pypi/whl_extract/BUILD.bazel b/tests/pypi/whl_extract/BUILD.bazel
new file mode 100644
index 0000000000..3983477f2b
--- /dev/null
+++ b/tests/pypi/whl_extract/BUILD.bazel
@@ -0,0 +1,11 @@
+load("@rules_shell//shell:sh_test.bzl", "sh_test")
+load(":whl_extract_tests.bzl", "whl_extract_test_suite")
+
+whl_extract_test_suite(name = "whl_extract_tests")
+
+sh_test(
+    name = "wheel_record_rewriter_test",
+    srcs = ["wheel_record_rewriter_test.sh"],
+    args = ["$(location //python/private/pypi:wheel_record_rewriter)"],
+    data = ["//python/private/pypi:wheel_record_rewriter"],
+)
diff --git a/tests/pypi/whl_extract/wheel_record_rewriter_test.sh b/tests/pypi/whl_extract/wheel_record_rewriter_test.sh
new file mode 100755
index 0000000000..c5880520ad
--- /dev/null
+++ b/tests/pypi/whl_extract/wheel_record_rewriter_test.sh
@@ -0,0 +1,91 @@
+#!/bin/sh
+set -eu
+
+REWRITER="$1"
+TMP_DIR="$(mktemp -d)"
+trap 'rm -rf "$TMP_DIR"' EXIT
+
+run_rewriter() {
+  case "$REWRITER" in
+    *.ps1)
+      in_file="$1"
+      out_file="$2"
+      platform_type="$3"
+      data_dir="$4"
+      if command -v cygpath >/dev/null 2>&1; then
+        in_file="$(cygpath -w "$in_file")"
+        out_file="$(cygpath -w "$out_file")"
+      fi
+      powershell.exe -ExecutionPolicy Bypass -NoProfile -File "$REWRITER" "$in_file" "$out_file" "$platform_type" "$data_dir"
+      ;;
+    *)
+      "$REWRITER" "$@"
+      ;;
+  esac
+}
+
+INPUT="$TMP_DIR/input_RECORD"
+cat <<'EOF' > "$INPUT"
+foo-1.0.data/purelib/pkg/__init__.py,sha256=abc,100
+foo-1.0.data/purelib/pkg/module.py,sha256=def,200
+foo-1.0.data/platlib/pkg/_ext.so,sha256=ghi,300
+foo-1.0.data/data/pkg/data.txt,sha256=111,10
+foo-1.0.data/headers/pkg/header.h,sha256=222,20
+foo-1.0.data/scripts/my_script.sh,sha256=333,30
+"foo-1.0.data/purelib/pkg/my file.py",sha256=abc,100
+"foo-1.0.data/scripts/my tool",sha256=def,200
+"foo-1.0.data/headers/my header.h",sha256=ghi,300
+"foo-1.0.data/data/my data.txt",sha256=jkl,400
+foo-1.0.data/custom_dir/custom.txt,sha256=xyz,123
+top_level/__init__.py,sha256=aaa,50
+foo-1.0.dist-info/METADATA,sha256=bbb,60
+foo-1.0.dist-info/RECORD,,
+EOF
+
+# Test Unix rewrite
+UNIX_OUT="$TMP_DIR/unix_RECORD"
+run_rewriter "$INPUT" "$UNIX_OUT" "unix" "foo-1.0.data"
+
+EXPECTED_UNIX="$TMP_DIR/expected_unix"
+cat <<'EOF' > "$EXPECTED_UNIX"
+pkg/__init__.py,sha256=abc,100
+pkg/module.py,sha256=def,200
+pkg/_ext.so,sha256=ghi,300
+../../../pkg/data.txt,sha256=111,10
+../../../include/pkg/header.h,sha256=222,20
+../../../bin/my_script.sh,sha256=333,30
+"pkg/my file.py",sha256=abc,100
+"../../../bin/my tool",sha256=def,200
+"../../../include/my header.h",sha256=ghi,300
+"../../../my data.txt",sha256=jkl,400
+foo-1.0.data/custom_dir/custom.txt,sha256=xyz,123
+top_level/__init__.py,sha256=aaa,50
+foo-1.0.dist-info/METADATA,sha256=bbb,60
+foo-1.0.dist-info/RECORD,,
+EOF
+
+diff -u --strip-trailing-cr "$EXPECTED_UNIX" "$UNIX_OUT"
+
+# Test Windows rewrite
+WIN_OUT="$TMP_DIR/win_RECORD"
+run_rewriter "$INPUT" "$WIN_OUT" "windows" "foo-1.0.data"
+
+EXPECTED_WIN="$TMP_DIR/expected_win"
+cat <<'EOF' > "$EXPECTED_WIN"
+pkg/__init__.py,sha256=abc,100
+pkg/module.py,sha256=def,200
+pkg/_ext.so,sha256=ghi,300
+../../pkg/data.txt,sha256=111,10
+../../Include/pkg/header.h,sha256=222,20
+../../Scripts/my_script.sh,sha256=333,30
+"pkg/my file.py",sha256=abc,100
+"../../Scripts/my tool",sha256=def,200
+"../../Include/my header.h",sha256=ghi,300
+"../../my data.txt",sha256=jkl,400
+foo-1.0.data/custom_dir/custom.txt,sha256=xyz,123
+top_level/__init__.py,sha256=aaa,50
+foo-1.0.dist-info/METADATA,sha256=bbb,60
+foo-1.0.dist-info/RECORD,,
+EOF
+
+diff -u --strip-trailing-cr "$EXPECTED_WIN" "$WIN_OUT"
diff --git a/tests/pypi/whl_extract/whl_extract_tests.bzl b/tests/pypi/whl_extract/whl_extract_tests.bzl
new file mode 100644
index 0000000000..f7e1e6d2cf
--- /dev/null
+++ b/tests/pypi/whl_extract/whl_extract_tests.bzl
@@ -0,0 +1,119 @@
+"""Tests for whl_extract and gen_wheel_record."""
+
+load("@rules_testing//lib:analysis_test.bzl", "analysis_test")
+load("@rules_testing//lib:test_suite.bzl", "test_suite")
+load("@rules_testing//lib:util.bzl", rt_util = "util")
+load(
+    "//python/private/pypi:gen_wheel_record.bzl",  # buildifier: disable=bzl-visibility
+    "gen_wheel_record",
+)
+load(
+    "//tests/support/platforms:platforms.bzl",  # buildifier: disable=bzl-visibility
+    "platform_targets",
+)
+
+_tests = []
+
+def _test_gen_wheel_record(name):
+    rt_util.helper_target(
+        native.genrule,
+        name = name + "_src",
+        outs = [name + "_orig/alpha-1.0.dist-info/RECORD"],
+        cmd = "echo 'alpha-1.0.data/scripts/foo.sh' > $@",
+    )
+    rt_util.helper_target(
+        gen_wheel_record,
+        name = name + "_subject",
+        srcs = [":" + name + "_src"],
+    )
+    analysis_test(
+        name = name,
+        target = name + "_subject",
+        impl = _test_gen_wheel_record_impl,
+    )
+
+_tests.append(_test_gen_wheel_record)
+
+def _test_gen_wheel_record_impl(env, target):
+    files = target[DefaultInfo].files.to_list()
+    env.expect.that_collection(files).has_size(1)
+    env.expect.that_str(files[0].short_path).contains(
+        "site-packages/alpha-1.0.dist-info/RECORD",
+    )
+
+def _test_gen_wheel_record_windows(name):
+    rt_util.helper_target(
+        native.genrule,
+        name = name + "_src",
+        outs = [name + "_orig/beta-1.0.dist-info/RECORD"],
+        cmd = "echo 'beta-1.0.data/scripts/foo.sh' > $@",
+    )
+    rt_util.helper_target(
+        gen_wheel_record,
+        name = name + "_subject",
+        srcs = [":" + name + "_src"],
+    )
+    analysis_test(
+        name = name,
+        target = name + "_subject",
+        config_settings = {
+            "//command_line_option:platforms": [
+                platform_targets.WINDOWS_X86_64,
+            ],
+        },
+        impl = _test_gen_wheel_record_windows_impl,
+    )
+
+_tests.append(_test_gen_wheel_record_windows)
+
+def _test_gen_wheel_record_windows_impl(env, target):
+    files = target[DefaultInfo].files.to_list()
+    env.expect.that_collection(files).has_size(1)
+    env.expect.that_str(files[0].short_path).contains(
+        "site-packages/beta-1.0.dist-info/RECORD",
+    )
+
+def _test_gen_wheel_record_multiple_srcs(name):
+    rt_util.helper_target(
+        native.genrule,
+        name = name + "_src1",
+        outs = [name + "_orig1/gamma-1.0.dist-info/RECORD"],
+        cmd = "echo 'gamma-1.0.data/scripts/foo.sh' > $@",
+    )
+    rt_util.helper_target(
+        native.genrule,
+        name = name + "_src2",
+        outs = [name + "_orig2/delta-2.0.dist-info/RECORD"],
+        cmd = "echo 'delta-2.0.data/scripts/bar.sh' > $@",
+    )
+    rt_util.helper_target(
+        gen_wheel_record,
+        name = name + "_subject",
+        srcs = [":" + name + "_src1", ":" + name + "_src2"],
+    )
+    analysis_test(
+        name = name,
+        target = name + "_subject",
+        impl = _test_gen_wheel_record_multiple_srcs_impl,
+    )
+
+_tests.append(_test_gen_wheel_record_multiple_srcs)
+
+def _test_gen_wheel_record_multiple_srcs_impl(env, target):
+    files = target[DefaultInfo].files.to_list()
+    env.expect.that_collection(files).has_size(2)
+    paths = [f.short_path for f in files]
+    env.expect.that_bool(
+        any(["site-packages/gamma-1.0.dist-info/RECORD" in p for p in paths]),
+    ).equals(True)
+    env.expect.that_bool(
+        any(["site-packages/delta-2.0.dist-info/RECORD" in p for p in paths]),
+    ).equals(True)
+
+def whl_extract_test_suite(name):
+    """Create the test suite.
+
+    Args:
+        name: the name of the test suite
+    """
+    test_suite(name = name, tests = _tests)
diff --git a/tests/pypi/whl_library_targets/whl_library_targets_tests.bzl b/tests/pypi/whl_library_targets/whl_library_targets_tests.bzl
index d752159b32..3fe1b99768 100644
--- a/tests/pypi/whl_library_targets/whl_library_targets_tests.bzl
+++ b/tests/pypi/whl_library_targets/whl_library_targets_tests.bzl
@@ -30,7 +30,7 @@ def _test_filegroups(env):
     def glob(include, *, exclude = [], allow_empty):
         _ = exclude  # @unused
         env.expect.that_bool(allow_empty).equals(True)
-        if include == ["rewrite-bin/*"] or include == ["bin/*"]:
+        if include in [["rewrite-bin/*"], ["bin/*"], ["rewrite-record/*/RECORD"]]:
             return []
         return include
 
@@ -42,6 +42,7 @@ def _test_filegroups(env):
         ),
         rules = struct(
             venv_rewrite_shebang = lambda **kwargs: None,
+            gen_wheel_record = lambda **kwargs: None,
         ),
     )
 
@@ -84,6 +85,7 @@ def _test_copy(env):
         rules = struct(
             copy_file = lambda **kwargs: calls.append(kwargs),
             venv_rewrite_shebang = lambda **kwargs: None,
+            gen_wheel_record = lambda **kwargs: None,
         ),
     )
 
@@ -242,6 +244,7 @@ def _test_sdist_excludes_record(env):
     m_glob = mocks.glob()
     m_glob.results.append([])  # bin
     m_glob.results.append([])  # rewrite-bin
+    m_glob.results.append([])  # rewrite-record
     m_glob.results.append([])  # srcs
     m_glob.results.append([])  # data
     m_glob.results.append([])  # pyi
@@ -259,6 +262,7 @@ def _test_sdist_excludes_record(env):
             py_library = lambda **kwargs: py_library_calls.append(kwargs),
             create_inits = lambda **kwargs: [],
             venv_rewrite_shebang = lambda **kwargs: None,
+            gen_wheel_record = lambda **kwargs: None,
         ),
     )
 
@@ -284,6 +288,7 @@ def _test_exclude_bazel_files(env):
         m_glob = mocks.glob()
         m_glob.results.append([])  # bin
         m_glob.results.append([])  # rewrite-bin
+        m_glob.results.append([])  # rewrite-record
         m_glob.results.append([])  # extracted_whl_files
         m_glob.results.append([])  # dist_info
         m_glob.results.append([])  # data
@@ -297,6 +302,7 @@ def _test_exclude_bazel_files(env):
             ),
             rules = struct(
                 venv_rewrite_shebang = lambda **kwargs: None,
+                gen_wheel_record = lambda **kwargs: None,
             ),
         )
 
@@ -314,6 +320,7 @@ def _test_exclude_bazel_files(env):
         env.expect.that_collection(m_glob.calls).contains_exactly([
             mocks.glob_call(["bin/*"], allow_empty = True),
             mocks.glob_call(["rewrite-bin/*"], allow_empty = True),
+            mocks.glob_call(["rewrite-record/*/RECORD"], allow_empty = True),
             mocks.glob_call(
                 include = ["**"],
                 exclude = expected_exclude,
diff --git a/tests/venv_site_packages_libs/importlib_metadata_test.py b/tests/venv_site_packages_libs/importlib_metadata_test.py
index 963d43b6e0..8e73b53141 100644
--- a/tests/venv_site_packages_libs/importlib_metadata_test.py
+++ b/tests/venv_site_packages_libs/importlib_metadata_test.py
@@ -1,4 +1,5 @@
 import importlib.metadata
+import sys
 import unittest
 
 
@@ -10,13 +11,66 @@ def test_importlib_metadata_files(self):
             len(files), 0, "importlib.metadata.files returned empty list"
         )
 
-        # Verify it contains some expected files.
-        # The RECORD file lists paths relative to the installation root (site-packages).
-        # whl_with_data1-1.0.data/purelib/data_overlap.py should be installed as data_overlap.py
-        # whl_with_data1-1.0.data/platlib/whl_with_data1/platlib_file.txt should be whl_with_data1/platlib_file.txt
+        if sys.platform == "win32":
+            scripts_prefix = "../../Scripts/"
+            headers_prefix = "../../Include/"
+            data_prefix = "../../"
+        else:
+            scripts_prefix = "../../../bin/"
+            headers_prefix = "../../../include/"
+            data_prefix = "../../../"
 
-        file_names = [f.name for f in files]
-        self.assertIn("data_overlap.py", file_names)
+        expected_paths = sorted(
+            [
+                scripts_prefix + "data_overlap.sh",
+                data_prefix + "bin/data_overlap.sh",
+                scripts_prefix + "overlap/both.sh",
+                scripts_prefix + "overlap/script1.sh",
+                scripts_prefix + "whl_script.sh",
+                scripts_prefix + "whl_with_data1_script",
+                headers_prefix + "data_overlap.h",
+                data_prefix + "include/data_overlap.h",
+                headers_prefix + "overlap/both.h",
+                headers_prefix + "overlap/header1.h",
+                headers_prefix + "whl_with_data1/header_file.h",
+                data_prefix + "overlap/both.txt",
+                data_prefix + "overlap/data1.txt",
+                data_prefix + "site-packages/data_overlap.py",
+                data_prefix + "whl_with_data1/data_data_file.txt",
+                data_prefix + "whl_with_data1/data_data_file.txt",
+                "data_overlap.py",
+                "whl_with_data1/data_file.txt",
+                "whl_with_data1/platlib_file.txt",
+            ]
+        )
+        file_paths = sorted(str(f).replace("\\", "/") for f in files)
+        self.assertEqual(file_paths, expected_paths)
+
+        for f in files:
+            resolved = f.locate()
+            if resolved.exists():
+                self.assertTrue(
+                    resolved.is_file(),
+                    f"Expected {resolved} to be a regular file",
+                )
+
+                # Verify file content can be read both as binary and as text
+                content = f.read_binary()
+                self.assertIsNotNone(content)
+
+                text = f.read_text(encoding="utf-8")
+                self.assertIsNotNone(text)
+            else:
+                # On Windows, venv bin scripts have a .bat extension appended.
+                bat_resolved = resolved.parent / (resolved.name + ".bat")
+                self.assertTrue(
+                    bat_resolved.exists(),
+                    f"Expected file {f} (resolved to {resolved} or {bat_resolved}) to exist",
+                )
+                self.assertTrue(
+                    bat_resolved.is_file(),
+                    f"Expected {bat_resolved} to be a regular file",
+                )
 
 
 if __name__ == "__main__":