Checklist is unable to be completed for Simple Sites

[dougaitken]

Steps to reproduce

1. Starting at URL: https://wordpress.com/stats/day/doug.blog
2. Note the Checklist, "update site icon"
3. Pressing "do it" and then return to checklist doesn't complete the item
4. Rechoosing the same image from my media library following the prompts it shows complete
5. Click link to Checklist - checkbox didn't show complete
6. Refresh page, Site Icon is check and moved position in the list
7. Update site tagline. Not all themes use a tagline and I don't use one for my site. I cannot bypass this

What I expected

To be able to bypass steps I had already completed.

What happened instead

I was unable to bypass any steps I had already complete.

My URL changed to my site ID after going through any part of the checklist. i.e. it no longer showed https://wordpress.com/stats/day/doug.blog but https://wordpress.com/stats/day/[site_id]

I "tricked" the flow by putting in a temporary tagline, saving, then going back, deleting it, and saving the page again. The checklist remained complete.
I haven't been able to check the final list item (Customize Contact page) at all.

Browser / OS version

Chrome Version 68.0.3440.106 (Official Build) (64-bit)
macOS 10.13.6 (17G65)

Context / Source

Context - was testing out #26870

[rossanafmenezes]

Other user reports with checklist saying they have not completed items that have already been completed on the site:

• #5740497-hc Same issue as Doug. Not able to finalize the last item.
• #1368907-zen - This checklist is stuck before that on Step 5

Both are pre-existing sites.

[dougaitken]

To confirm - manually checking the boxes does work.

FWIW I was stuck on Step 5 @rossanafmenezes . ... I just added the same image back as the site icon 🙈

[sirreal]

I've just followed the steps in the tour to update the site icon and it did work.

However, it initially reported the task as incomplete. This may simply be the server taking some time to update the checklist task status. We return to the checklist and query the data before the server is updated, so the client gets stale data and is incorrectly shown the just completed step.

[mattwiebe]

Older sites would not have had their checklist properly initialized which meant that nothing would get checked off properly. I believe that completing an item manually would have done the initialization and therefore the list would have started working as expected, but simply following the Guided Tour steps would not have. Now that #26867 has landed, older sites will simply not see the checklist. We'll have to figure out that initialization logic should we wish to deploy the checklist to them, too.