diff --git a/lib/fs.js b/lib/fs.js
index ace5c464b73b14..78f931060742ad 100644
--- a/lib/fs.js
+++ b/lib/fs.js
@@ -2730,9 +2730,21 @@ function realpathSync(p, options) {
   // Walk down the path, swapping out linked path parts for their real
   // values
   // NB: p.length changes.
-  while (pos < p.length) {
-    // find the next part
-    const result = nextPart(p, pos);
+  let unresolvedTail = '';
+  while (true) {
+    if (pos >= p.length) {
+      if (unresolvedTail === '') {
+        break;
+      }
+
+      p = pathModule.resolve(p + unresolvedTail);
+      unresolvedTail = '';
+      current = base = splitRoot(p);
+      pos = current.length;
+      continue;
+    }
+
+    const result = nextPart(p + unresolvedTail, pos);
     previous = current;
     if (result === -1) {
       const last = StringPrototypeSlice(p, pos);
@@ -2740,7 +2752,7 @@ function realpathSync(p, options) {
       base = previous + last;
       pos = p.length;
     } else {
-      current += StringPrototypeSlice(p, pos, result + 1);
+      current += StringPrototypeSlice(p + unresolvedTail, pos, result + 1);
       base = previous + StringPrototypeSlice(p, pos, result);
       pos = result + 1;
     }
@@ -2761,7 +2773,6 @@ function realpathSync(p, options) {
     } else {
       // Use stats array directly to avoid creating an fs.Stats instance just
       // for our internal use.
-
       const stats = binding.lstat(base, true, undefined, true /* throwIfNoEntry */);
       if (stats === undefined) {
         return;
@@ -2770,6 +2781,11 @@ function realpathSync(p, options) {
       if (!isFileType(stats, S_IFLNK)) {
         knownHard.add(base);
         cache?.set(base, base);
+        if (unresolvedTail !== '') {
+          p = pathModule.resolve(p + unresolvedTail);
+          unresolvedTail = '';
+        }
+
         continue;
       }
 
@@ -2789,8 +2805,14 @@ function realpathSync(p, options) {
         binding.stat(base, false, undefined, true);
         linkTarget = binding.readlink(base, undefined);
       }
-      resolvedLink = pathModule.resolve(previous, linkTarget);
 
+      const nextPathDelimiterIndex = nextPart(linkTarget, 0);
+      if (nextPathDelimiterIndex >= 1) {
+        unresolvedTail = StringPrototypeSlice(linkTarget, nextPathDelimiterIndex) + unresolvedTail;
+        linkTarget = StringPrototypeSlice(linkTarget, 0, nextPathDelimiterIndex);
+      }
+
+      resolvedLink = pathModule.resolve(previous, linkTarget);
       cache?.set(base, resolvedLink);
       if (!isWindows) seenLinks.set(id, linkTarget);
     }
diff --git a/test/parallel/test-fs-realpath-dotdot-symlink.js b/test/parallel/test-fs-realpath-dotdot-symlink.js
new file mode 100644
index 00000000000000..bc44dd7846620b
--- /dev/null
+++ b/test/parallel/test-fs-realpath-dotdot-symlink.js
@@ -0,0 +1,30 @@
+'use strict';
+
+const fs = require('fs');
+const path = require('path');
+const assert = require('assert');
+
+const common = require('../common');
+const tmpdir = require('../common/tmpdir');
+
+if (common.isWindows) {
+  common.skip('symlink semantics differ on Windows');
+}
+
+tmpdir.refresh();
+
+const cwd = path.join(tmpdir.path, 'test');
+fs.mkdirSync(path.join(cwd, 'a', 'b', 'c'), { recursive: true });
+fs.mkdirSync(path.join(cwd, 'a', 'b', 'd'), { recursive: true });
+
+process.chdir(cwd);
+
+// ln -s a/b/c c
+fs.symlinkSync('a/b/c', 'c', 'dir');
+// ln -s "c/../d" d
+fs.symlinkSync('c/../d', 'd', 'dir');
+
+const expected = path.resolve(path.join(cwd, 'a', 'b', 'd'));
+
+// sync
+assert.strictEqual(fs.realpathSync('d'), expected);