diff --git a/core/commands/add.go b/core/commands/add.go
index 90861302551..73491c03b44 100644
--- a/core/commands/add.go
+++ b/core/commands/add.go
@@ -288,6 +288,10 @@ See 'dag export' and 'dag import' for more information.
 			return fmt.Errorf("%s and %s options are not compatible", onlyHashOptionName, toFilesOptionName)
 		}
 
+		if wrap && toFilesSet {
+			return fmt.Errorf("%s and %s options are not compatible", wrapOptionName, toFilesOptionName)
+		}
+
 		hashFunCode, ok := mh.Names[strings.ToLower(hashFunStr)]
 		if !ok {
 			return fmt.Errorf("unrecognized hash function: %q", strings.ToLower(hashFunStr))
@@ -373,6 +377,11 @@ See 'dag export' and 'dag import' for more information.
 
 				// creating MFS pointers when optional --to-files is set
 				if toFilesSet {
+					if addit.Name() == "" {
+						errCh <- fmt.Errorf("%s: cannot add unnamed files to MFS", toFilesOptionName)
+						return
+					}
+
 					if toFilesStr == "" {
 						toFilesStr = "/"
 					}
diff --git a/docs/changelogs/v0.33.md b/docs/changelogs/v0.33.md
index a5d8ef2ef34..1adf16dd0bb 100644
--- a/docs/changelogs/v0.33.md
+++ b/docs/changelogs/v0.33.md
@@ -6,6 +6,9 @@
 
 - [Overview](#overview)
 - [🔦 Highlights](#-highlights)
+  - [Bitswap improvements from Boxo](#bitswap-improvements-from-boxo)
+  - [Using default `libp2p_rcmgr`  metrics](#using-default-libp2p_rcmgr--metrics)
+  - [`ipfs add --to-files` no longer works with `--wrap`](#ipfs-add---to-files-no-longer-works-with---wrap)
   - [📦️ Dependency updates](#-dependency-updates)
 - [📝 Changelog](#-changelog)
 - [👨‍👩‍👧‍👦 Contributors](#-contributors)
@@ -24,6 +27,10 @@ Bespoke rcmgr metrics [were removed](https://github.com/ipfs/kubo/pull/9947), Ku
 This makes it easier to compare Kubo with custom implementations based on go-libp2p.
 If you depended on removed ones, please fill an issue to add them to the upstream [go-libp2p](https://github.com/libp2p/go-libp2p).
 
+#### `ipfs add --to-files` no longer works with `--wrap`
+
+Onboarding files and directories with `ipfs add --to-files` now requires non-empty names. due to this, The `--to-files` and `--wrap` options are now mutually exclusive ([#10612](https://github.com/ipfs/kubo/issues/10612)).
+
 #### 📦️ Dependency updates
 
 - update `boxo` to [v0.24.TODO](https://github.com/ipfs/boxo/releases/tag/v0.24.TODO)
diff --git a/test/sharness/t0040-add-and-cat.sh b/test/sharness/t0040-add-and-cat.sh
index 142ab8ec18c..c7232bedd8c 100755
--- a/test/sharness/t0040-add-and-cat.sh
+++ b/test/sharness/t0040-add-and-cat.sh
@@ -355,10 +355,10 @@ test_add_cat_file() {
     test_cmp expected actual
   '
 
-    test_must_fail "ipfs add with multiple files of same name but different dirs fails" '
+    test_expect_success "ipfs add with multiple files of same name but different dirs fails" '
       mkdir -p mountdir/same-file/ &&
       cp mountdir/hello.txt mountdir/same-file/hello.txt &&
-      ipfs add mountdir/hello.txt mountdir/same-file/hello.txt >actual &&
+      test_expect_code 1 ipfs add mountdir/hello.txt mountdir/same-file/hello.txt >actual &&
       rm mountdir/same-file/hello.txt  &&
       rmdir mountdir/same-file
     '
@@ -469,6 +469,15 @@ test_add_cat_file() {
     ipfs files rm -r --force /mfs
   '
 
+  # confirm -w and --to-files are exclusive
+  # context: https://github.com/ipfs/kubo/issues/10611
+  test_expect_success "ipfs add -r -w dir --to-files /mfs/subdir5/ errors (-w and --to-files are exclusive)" '
+    ipfs files mkdir -p /mfs/subdir5 &&
+    test_expect_code 1 ipfs add -r -w test --to-files /mfs/subdir5/ >actual 2>&1 &&
+    test_should_contain "Error" actual &&
+    ipfs files rm -r --force /mfs
+  '
+
 }
 
 test_add_cat_5MB() {