Smilies not converted when directly followed by punctuation marks

[ourvalley]

Steps to recreate:

• Create a new post or comment
• Insert a smilie directly followed by a period or other punctuation mark such as :).
• View the post or comment

Expected:

Ideally the smilie would show followed by the punctuation mark.

I've attached a screenshot showing how a post with the following text appears. Smiles with a space between them and the punctuation mark show, but the others do not.

This is a test :). It uses smilies :)

If a smilie has punctuation directly after, it is not converted :(! :(

The expected behavior would be to look like this:
:) ! :) ,
However instead they appear as this
:)! :),

[costdev]

Reproduction Report

Env

• WordPress: 6.0-alpha-52448-src
• Chrome 97.0.4692.71
• Windows 10
• Theme: Twenty Twenty-Two
• Block Editor
• Plugins: None activated

Steps to reproduce

1. Navigate to Posts > Add New.
2. Paste the following as plain text:

   This is a test :). It uses smilies :)
   
   If a smilie has punctuation directly after, it is not converted :(! :(
   
   The expected behavior would be to look like this:
   :) ! :) ,
   However instead they appear as this
   :)! :),
   

3. Click "Publish".
4. Click "View post".
5. You should see that only 4 of the 8 emoticons will be converted to smilies.

Results

Reproduced.

However, this is actually intended behaviour. The code that does the substitution specifically looks for spaces before converting an emoticon to a smiley. Therefore, this is not a defect (bug).

A quick search online suggests that this appears to have been a pain point for users for quite some years. For this reason, I'm marking this as an enhancement and adding it to the 6.0 milestone for visibility and discussion.

[costdev]

Per the discussion in the bug scrub, I'm adding 2nd-opinion to attract discussion on whether this change is desired.

Regarding the expected behaviour, ​see here.

[peterwilsoncc]

As this lacks a patch and is need of a second opinion, I'll move it off the 6.0 milestone.