diff --git a/runtime/vscode/overrides/vscode-window-commands.vim b/runtime/vscode/overrides/vscode-window-commands.vim
index 824bd29..adf4d53 100644
--- a/runtime/vscode/overrides/vscode-window-commands.vim
+++ b/runtime/vscode/overrides/vscode-window-commands.vim
@@ -34,6 +34,14 @@ function! s:manageEditorWidth(...)
     endfor
 endfunction
 
+" A lone <C-w> runs the builtin window command once 'timeoutlen' passes, and that reads the next key
+" without mappings, skipping the ones below. Read the key here instead and feed the whole command
+" again, remapped when one of them handles it.
+function! s:windowCommand(mode) abort
+    let keys = "\<C-w>" . getcharstr()
+    call feedkeys((v:count ? v:count : '') . keys, (empty(maparg(keytrans(keys), a:mode)) ? 'n' : 'm') . 'i')
+endfunction
+
 command! -complete=file -nargs=? Split call <SID>split('h', <q-args>)
 command! -complete=file -nargs=? Vsplit call <SID>split('v', <q-args>)
 command! -complete=file -nargs=? New call <SID>split('h', '__vscode_new__')
@@ -46,6 +54,9 @@ AlterCommand new New
 AlterCommand vne[w] Vnew
 AlterCommand on[ly] Only
 
+nnoremap <C-w> <Cmd>call <SID>windowCommand('n')<CR>
+xnoremap <C-w> <Cmd>call <SID>windowCommand('x')<CR>
+
 " buffer management
 nnoremap <C-w>n <Cmd>call <SID>splitNew('h', '__vscode_new__')<CR>
 xnoremap <C-w>n <Cmd>call <SID>splitNew('h', '__vscode_new__')<CR>
diff --git a/src/test/integ/vscode-integration-specific.test.ts b/src/test/integ/vscode-integration-specific.test.ts
index 25bb56e..5133149 100644
--- a/src/test/integ/vscode-integration-specific.test.ts
+++ b/src/test/integ/vscode-integration-specific.test.ts
@@ -6,7 +6,7 @@ import { strict as assert } from "assert";
 import vscode, { Selection } from "vscode";
 import { NeovimClient } from "neovim";
 
-import { wait } from "../../utils";
+import { wait, waitUntil } from "../../utils";
 
 import {
     attachTestNvimClient,
@@ -345,6 +345,22 @@ describe("VSCode integration specific stuff", () => {
         );
     });
 
+    it("Window commands typed after timeoutlen still go to vscode #2466", async () => {
+        await openTextDocument({ content: "blah" });
+        const timeoutlen = (await client.getOption("timeoutlen")) as number;
+        await client.setOption("timeoutlen", 100);
+        try {
+            await sendNeovimKeys(client, "<C-w>", 500);
+            await sendNeovimKeys(client, "v");
+            await waitUntil(() =>
+                assert.equal(vscode.window.tabGroups.all.length, 2, "<C-w>v should split the editor"),
+            );
+        } finally {
+            await client.setOption("timeoutlen", timeoutlen);
+            await vscode.commands.executeCommand("workbench.action.joinAllGroups");
+        }
+    });
+
     it("Opens a file through e command", async () => {
         const filePath = path.join(os.tmpdir(), Math.random().toString());
         fs.writeFileSync(filePath, ["line 1"].join("\n"), {