@Axelwren
Using Perplexity.ai, and search criteria:
chrome menu in windows taskbar will not open private window
The Perplexity.ai results:
On Windows, the “New incognito/private window” option for Chrome on the taskbar usually disappears because of Windows jump list settings or a broken taskbar shortcut. The fixes below restore the private window option in most cases.
Quick checks
- Make sure you are right‑clicking the Chrome icon on the taskbar, then right‑clicking “Google Chrome” in the small menu that appears; that second right‑click is where “New window” and “New incognito window” normally show.
- If nothing shows except “Google Chrome” and “Unpin from taskbar”, the jump list is likely disabled at the Windows level.
Re‑enable Windows jump lists
- Open Settings → Personalization → Start.
- Turn On “Show recently opened items in Start, Jump Lists, and File Explorer” (wording may vary slightly between Windows 10/11).
- Use Chrome normally for a few minutes (open a regular window and an incognito window from the Chrome menu at the top right) and then close it.
- Right‑click the Chrome icon on the taskbar again and check if “New incognito window” has returned.reddit+1
If you previously disabled jump lists with a privacy or cleanup tool (for example, some scripts or cleaners can do this), re‑enabling this setting is essential for the menu to work.reddit
Recreate the taskbar shortcut
If the setting above is already on or does not help:
- Right‑click the Chrome icon on the taskbar and choose Unpin from taskbar.reddit+1
- Open Chrome from the Start menu or desktop shortcut.
- In Chrome, open an incognito window from the browser menu (three dots → New incognito window).reddit
- With Chrome open, right‑click the Chrome icon on the taskbar and select Pin to taskbar.reddit
- Close Chrome and then right‑click the new pinned icon on the taskbar to see if “New incognito window” now appears.overclockers+1
If it still does not work
- Check for any third‑party cleaners or “privacy” tools that might disable jump lists or clear the data Chrome uses for them, and disable that feature.brave+1
- If the problem persists across reboots even after the steps above, reinstalling Chrome and then pinning it again from a freshly opened normal window often restores a proper jump list.level1techs
A fresh install, using the Brave Browser installers with highest potential for success with future updates:
In general, I favor a fresh, proper Brave Browser installation, that may solve the issue by eventually establishing a proper “connecting-of-the-dots” between the Brave Browser User Data and the Brave icon/item in the Windows Taskbar, in addition to a proper Brave Browser shortcut on the Desktop.
So, at: https://github.com/brave/brave-browser/blob/master/CHANGELOG_DESKTOP.md you would select: https://github.com/brave/brave-browser/releases/tag/v1.85.111
And then scroll down and select either of the following. The first, BraveBrowserSetup.exe is what Brave would prefer that you use. The second choice, would be better than a “standalone” installation.
Somewhere I read, that there is some caution re using the “standalone” versions (such as you found at GitHub) - they are intended for customized installations that are placed in locations that are not standard / not typical for most Brave Browser users.
But your Brave.exe path is a standard location (thankfully) (and thank you for improving your OP).
Now, what I would do, is probably different than your notion(s). I would stop Brave Sync (if using), disable all extensions, clear cache, cookies, history (for All time), Exit / Quit everything and Restart the computer.
Then backup my Brave Browser bookmarks, data, passwords - storing everything securely and NOT in a Brave Browser installation path.
Then un-install Brave Browser by using the https://crystalidea.com/uninstall-tool - followed by looking around for where some Brave items remained in the Brave Browser’s .exe installation path, somehow, and delete those, too.
Then Exit / Quit everything again, and Restart the computer. And then, use one of the two recommended installers (first choice: BraveBrowserSetup.exe) mentioned.
I would do all that, because I want to improve the chances for successful future updating of Brave Browser.
Create dedicated Brave Shortcuts on Desktop:
On the other hand, you might skip all that for now, and experiment. You could create 2 different Brave Browser shortcuts on your Desktop:
- 1st shortcut for starting Brave Browser with a standard, non-private New Window, and
- 2nd shortcut for starting Brave Browser with a Private New Window (–incognito).
For that 2nd Brave Browser New Private Window shortcut, you would change the path info: the switches are intended to:
- Start up Brave Browser, using the “Default” named user Profile folder [
--profile-directory="Default"]
- Showing a New Private Window [
--incognito]
So, x86 architecture, system level installation:
"C:\Program Files(x86)\BraveSoftware\Brave-Browser\Application\brave.exe" --profile-directory="Default" --incognito
Notice that the existing path, BEFORE the additions, is enclosed by double-quote marks:
"C:\Program Files(x86)\BraveSoftware\Brave-Browser\Application\brave.exe"
And, everything added to the existing path, is located after the existing path.
When running, use the Brave Browser’s 3-horizontal lines “hamburger” menu (upper right-hand corner of a Brave Browser window) in order to open a New Private Window).
Useful info: Where Brave Browser Profiles Are Located