diff --git a/deps/cares/cares.gyp b/deps/cares/cares.gyp
index 87898f5610d56c..c34ad7370ca45a 100644
--- a/deps/cares/cares.gyp
+++ b/deps/cares/cares.gyp
@@ -1,7 +1,9 @@
 {
   'variables': {
+    # This list is generated by `tools/dep_updaters/update-c-ares.mjs`.
     'cares_sources_common': [
       'include/ares.h',
+      'include/ares_build.h',
       'include/ares_dns.h',
       'include/ares_dns_record.h',
       'include/ares_nameser.h',
@@ -49,6 +51,8 @@
       'src/lib/ares_strerror.c',
       'src/lib/ares_sysconfig.c',
       'src/lib/ares_sysconfig_files.c',
+      'src/lib/ares_sysconfig_mac.c',
+      'src/lib/ares_sysconfig_win.c',
       'src/lib/ares_timeout.c',
       'src/lib/ares_update_servers.c',
       'src/lib/ares_version.c',
@@ -111,11 +115,11 @@
       'src/lib/record/ares_dns_private.h',
       'src/lib/record/ares_dns_record.c',
       'src/lib/record/ares_dns_write.c',
-      'src/lib/str/ares__buf.h',
       'src/lib/str/ares_buf.c',
       'src/lib/str/ares_str.c',
       'src/lib/str/ares_strsplit.c',
       'src/lib/str/ares_strsplit.h',
+      'src/lib/thirdparty/apple/dnsinfo.h',
       'src/lib/util/ares_iface_ips.c',
       'src/lib/util/ares_iface_ips.h',
       'src/lib/util/ares_math.c',
@@ -128,18 +132,10 @@
       'src/lib/util/ares_timeval.c',
       'src/lib/util/ares_uri.c',
       'src/lib/util/ares_uri.h',
-      'src/tools/ares_getopt.c',
-      'src/tools/ares_getopt.h',
+      'src/lib/windows_port.c',
     ],
     'cares_sources_mac': [
       'config/darwin/ares_config.h',
-      'src/lib/ares_sysconfig_mac.c',
-      'src/lib/thirdparty/apple/dnsinfo.h',
-    ],
-    'cares_sources_win': [
-      'src/lib/ares_sysconfig_win.c',
-      'src/lib/config-win32.h',
-      'src/lib/windows_port.c',
     ],
   },
 
@@ -201,9 +197,6 @@
             '_WINSOCK_DEPRECATED_NO_WARNINGS',
           ],
           'include_dirs': [ 'config/win32' ],
-          'sources': [
-            '<@(cares_sources_win)',
-          ],
           'libraries': [
             '-lws2_32.lib',
             '-liphlpapi.lib'
diff --git a/tools/dep_updaters/update-c-ares.mjs b/tools/dep_updaters/update-c-ares.mjs
new file mode 100644
index 00000000000000..c5057e666de70d
--- /dev/null
+++ b/tools/dep_updaters/update-c-ares.mjs
@@ -0,0 +1,38 @@
+// Synchronize the sources for our c-ares gyp file from c-ares' Makefiles.
+import { readFileSync, writeFileSync } from 'node:fs';
+import { join } from 'node:path';
+
+const srcroot = join(import.meta.dirname, '..', '..');
+const options = { encoding: 'utf8' };
+
+// Extract list of sources from the gyp file.
+const gypFile = join(srcroot, 'deps', 'cares', 'cares.gyp');
+const contents = readFileSync(gypFile, options);
+const sourcesRE = /^\s+'cares_sources_common':\s+\[\s*\n(?<files>[\s\S]*?)\s+\],$/gm;
+const sourcesCommon = sourcesRE.exec(contents);
+
+// Extract the list of sources from c-ares' Makefile.inc.
+const makefile = join(srcroot, 'deps', 'cares', 'src', 'lib', 'Makefile.inc');
+const libSources = readFileSync(makefile, options).split('\n')
+  // Extract filenames (excludes comments and variable assignment).
+  .map((line) => line.match(/^(?:.*= |\s*)?([^#\s]*)\s*\\?/)?.[1])
+  // Filter out empty lines.
+  .filter((line) => line !== '')
+  // Prefix with directory and format as list entry.
+  .map((line) => `      'src/lib/${line}',`);
+
+// Extract include files.
+const includeMakefile = join(srcroot, 'deps', 'cares', 'include', 'Makefile.am');
+const includeSources = readFileSync(includeMakefile, options)
+  .match(/include_HEADERS\s*=\s*(.*)/)[1]
+  .split(/\s/)
+  .map((header) => `      'include/${header}',`);
+
+// Combine the lists. Alphabetically sort to minimize diffs.
+const fileList = includeSources.concat(libSources).sort();
+
+// Replace the list of sources.
+const newContents = contents.replace(sourcesCommon.groups.files, fileList.join('\n'));
+if (newContents !== contents) {
+  writeFileSync(gypFile, newContents, options);
+}
diff --git a/tools/dep_updaters/update-c-ares.sh b/tools/dep_updaters/update-c-ares.sh
index 66d37ba350c246..f990430d9f6aee 100755
--- a/tools/dep_updaters/update-c-ares.sh
+++ b/tools/dep_updaters/update-c-ares.sh
@@ -71,6 +71,9 @@ cp "$DEPS_DIR/cares/"*.gn "$DEPS_DIR/cares/"*.gni "$WORKSPACE/cares"
 echo "Replacing existing c-ares"
 replace_dir "$DEPS_DIR/cares" "$WORKSPACE/cares"
 
+echo "Updating cares.gyp"
+"$NODE" "$ROOT/tools/dep_updaters/update-c-ares.mjs"
+
 # Update the version number on maintaining-dependencies.md
 # and print the new version as the last line of the script as we need
 # to add it to $GITHUB_ENV variable