diff --git a/Documentation/filesystems/overlayfs.rst b/Documentation/filesystems/overlayfs.rst
index 580ab9a0fe31..137afeb3f581 100644
--- a/Documentation/filesystems/overlayfs.rst
+++ b/Documentation/filesystems/overlayfs.rst
@@ -575,6 +575,14 @@ without significant effort.
 The advantage of mounting with the "volatile" option is that all forms of
 sync calls to the upper filesystem are omitted.
 
+In order to avoid a giving a false sense of safety, the syncfs (and fsync)
+semantics of volatile mounts are slightly different than that of the rest of
+VFS.  If any writeback error occurs on the upperdir's filesystem after a
+volatile mount takes place, all sync functions will return an error.  Once this
+condition is reached, the filesystem will not recover, and every subsequent sync
+call will return an error, even if the upperdir has not experience a new error
+since the last sync call.
+
 When overlay is mounted with "volatile" option, the directory
 "$workdir/work/incompat/volatile" is created.  During next mount, overlay
 checks for this directory and refuses to mount if present. This is a strong
diff --git a/fs/overlayfs/file.c b/fs/overlayfs/file.c
index a1f72ac053e5..5c5c3972ebd0 100644
--- a/fs/overlayfs/file.c
+++ b/fs/overlayfs/file.c
@@ -445,8 +445,9 @@ static int ovl_fsync(struct file *file, loff_t start, loff_t end, int datasync)
 	const struct cred *old_cred;
 	int ret;
 
-	if (!ovl_should_sync(OVL_FS(file_inode(file)->i_sb)))
-		return 0;
+	ret = ovl_sync_status(OVL_FS(file_inode(file)->i_sb));
+	if (ret <= 0)
+		return ret;
 
 	ret = ovl_real_fdget_meta(file, &real, !datasync);
 	if (ret)
diff --git a/fs/overlayfs/overlayfs.h b/fs/overlayfs/overlayfs.h
index f8880aa2ba0e..9f7af98ae200 100644
--- a/fs/overlayfs/overlayfs.h
+++ b/fs/overlayfs/overlayfs.h
@@ -322,6 +322,7 @@ int ovl_check_metacopy_xattr(struct ovl_fs *ofs, struct dentry *dentry);
 bool ovl_is_metacopy_dentry(struct dentry *dentry);
 char *ovl_get_redirect_xattr(struct ovl_fs *ofs, struct dentry *dentry,
 			     int padding);
+int ovl_sync_status(struct ovl_fs *ofs);
 
 static inline bool ovl_is_impuredir(struct super_block *sb,
 				    struct dentry *dentry)
diff --git a/fs/overlayfs/ovl_entry.h b/fs/overlayfs/ovl_entry.h
index 1b5a2094df8e..b208eba5d0b6 100644
--- a/fs/overlayfs/ovl_entry.h
+++ b/fs/overlayfs/ovl_entry.h
@@ -79,6 +79,8 @@ struct ovl_fs {
 	atomic_long_t last_ino;
 	/* Whiteout dentry cache */
 	struct dentry *whiteout;
+	/* r/o snapshot of upperdir sb's only taken on volatile mounts */
+	errseq_t errseq;
 };
 
 static inline struct vfsmount *ovl_upper_mnt(struct ovl_fs *ofs)
diff --git a/fs/overlayfs/readdir.c b/fs/overlayfs/readdir.c
index 01620ebae1bd..a273ef901e57 100644
--- a/fs/overlayfs/readdir.c
+++ b/fs/overlayfs/readdir.c
@@ -909,8 +909,9 @@ static int ovl_dir_fsync(struct file *file, loff_t start, loff_t end,
 	struct file *realfile;
 	int err;
 
-	if (!ovl_should_sync(OVL_FS(file->f_path.dentry->d_sb)))
-		return 0;
+	err = ovl_sync_status(OVL_FS(file->f_path.dentry->d_sb));
+	if (err <= 0)
+		return err;
 
 	realfile = ovl_dir_real_file(file, true);
 	err = PTR_ERR_OR_ZERO(realfile);
diff --git a/fs/overlayfs/super.c b/fs/overlayfs/super.c
index 290983bcfbb3..d23177a53c95 100644
--- a/fs/overlayfs/super.c
+++ b/fs/overlayfs/super.c
@@ -261,11 +261,20 @@ static int ovl_sync_fs(struct super_block *sb, int wait)
 	struct super_block *upper_sb;
 	int ret;
 
-	if (!ovl_upper_mnt(ofs))
-		return 0;
+	ret = ovl_sync_status(ofs);
+	/*
+	 * We have to always set the err, because the return value isn't
+	 * checked in syncfs, and instead indirectly return an error via
+	 * the sb's writeback errseq, which VFS inspects after this call.
+	 */
+	if (ret < 0) {
+		errseq_set(&sb->s_wb_err, -EIO);
+		return -EIO;
+	}
+
+	if (!ret)
+		return ret;
 
-	if (!ovl_should_sync(ofs))
-		return 0;
 	/*
 	 * Not called for sync(2) call or an emergency sync (SB_I_SKIP_SYNC).
 	 * All the super blocks will be iterated, including upper_sb.
@@ -1927,6 +1936,8 @@ static int ovl_fill_super(struct super_block *sb, void *data, int silent)
 	sb->s_op = &ovl_super_operations;
 
 	if (ofs->config.upperdir) {
+		struct super_block *upper_sb;
+
 		if (!ofs->config.workdir) {
 			pr_err("missing 'workdir'\n");
 			goto out_err;
@@ -1936,6 +1947,16 @@ static int ovl_fill_super(struct super_block *sb, void *data, int silent)
 		if (err)
 			goto out_err;
 
+		upper_sb = ovl_upper_mnt(ofs)->mnt_sb;
+		if (!ovl_should_sync(ofs)) {
+			ofs->errseq = errseq_sample(&upper_sb->s_wb_err);
+			if (errseq_check(&upper_sb->s_wb_err, ofs->errseq)) {
+				err = -EIO;
+				pr_err("Cannot mount volatile when upperdir has an unseen error. Sync upperdir fs to clear state.\n");
+				goto out_err;
+			}
+		}
+
 		err = ovl_get_workdir(sb, ofs, &upperpath);
 		if (err)
 			goto out_err;
@@ -1943,9 +1964,8 @@ static int ovl_fill_super(struct super_block *sb, void *data, int silent)
 		if (!ofs->workdir)
 			sb->s_flags |= SB_RDONLY;
 
-		sb->s_stack_depth = ovl_upper_mnt(ofs)->mnt_sb->s_stack_depth;
-		sb->s_time_gran = ovl_upper_mnt(ofs)->mnt_sb->s_time_gran;
-
+		sb->s_stack_depth = upper_sb->s_stack_depth;
+		sb->s_time_gran = upper_sb->s_time_gran;
 	}
 	oe = ovl_get_lowerstack(sb, splitlower, numlower, ofs, layers);
 	err = PTR_ERR(oe);
diff --git a/fs/overlayfs/util.c b/fs/overlayfs/util.c
index 23f475627d07..6e7b8c882045 100644
--- a/fs/overlayfs/util.c
+++ b/fs/overlayfs/util.c
@@ -950,3 +950,30 @@ char *ovl_get_redirect_xattr(struct ovl_fs *ofs, struct dentry *dentry,
 	kfree(buf);
 	return ERR_PTR(res);
 }
+
+/*
+ * ovl_sync_status() - Check fs sync status for volatile mounts
+ *
+ * Returns 1 if this is not a volatile mount and a real sync is required.
+ *
+ * Returns 0 if syncing can be skipped because mount is volatile, and no errors
+ * have occurred on the upperdir since the mount.
+ *
+ * Returns -errno if it is a volatile mount, and the error that occurred since
+ * the last mount. If the error code changes, it'll return the latest error
+ * code.
+ */
+
+int ovl_sync_status(struct ovl_fs *ofs)
+{
+	struct vfsmount *mnt;
+
+	if (ovl_should_sync(ofs))
+		return 1;
+
+	mnt = ovl_upper_mnt(ofs);
+	if (!mnt)
+		return 0;
+
+	return errseq_check(&mnt->mnt_sb->s_wb_err, ofs->errseq);
+}
