URI's What am I missing?

[gsam]

Broken URL = https://www.paddletramps.com/categor...l-Plaques.html
Correct URL = https://www.paddletramps.com/categor...l-Plaques.html

Opened the category and added a '301 Redirect to Canonical' clicked the save icon and then clicked the Regenerate button.

Screen Shot 2019-03-22 at 10.09.59 AM.png

Cleared my browser cache opened the URL and it still shows file not found.
Went to the URI Management and updated the .htaccess file.
Still, the URL shows file not found.
Opened the .htaccess file and could find no reference to the URL in question.

I must be missing something or doing something wrong?

[ILoveHostasaurus]

I believe the issue is your htaccess has the legacy short URL rewrites still in place, and before the URI management rewrites. Assuming your URI management data is fully populated, it should be safe to remove those legacy rewrites and allow URI management to take over.

[gsam]

That's it. Just like my customers, I don't read things closely. I had turned off the 'Enable SEO-Friendly Store Front' but missed the 'Enable Short Links'.

So, anytime I add or edit a URI do I need to click the Regenerate button and update the htaccess?