Automation to add a daily comment to assignees until a task is completed

Jeanine Lore Wrike doesn't have a built-in feature to annoy people via email, which could be helpful sometimes. 

You can trigger an action with the "status doesn't change in x days" but that only triggers once, not recurring. 

Here's another thought: create a status of "past due" in your workflow, then when the task goes past due, use your current automation to notify assignees and change the status to "past due." Then have a list of automation that triggers if the status doesn't change from "Past due" in 1, 2, 3, 4, 5, 6, 7, etc. days.

That should cause them to go back in the system and change the status to something else. 

As a safeguard, you could also have an automation that triggers when the status changes back to "in process" if the task is overdue then Wrike will change the status back to "past due". 

That would sufficiently annoy me 😂

We have a very similar scenario. It is not possible for us to use Wrike's Proofing/Approval tools (our team has to use Adobe-Workfront-ProofHQ, it's been acquired so many times it has 3 names, lol). We've explored using Zapier or something to integrate and make the 2 'talk' - unfortunately we have limitations on our side (and ProofHQ) that make that impossible.

Then scenario would make the process less manual, ProofHQ decision made -> triggers a comment or status change in Wrike. Since I can't do anything in ProofHQ's settings (controlled by admin ITs who won't allow), I can look into having the ProofHQ emails somehow sync to Wrike via an Outlook integration. It'll still be clunky but it's my next thought for helping connect the 2 dots.  

I know this isn't what you asked for - but hoping to paint the picture for how we're navigating the very awkward situation. And having to keep track of Approvals in 2 places is a paaaaaaaiiiiinnn, I know. FWIW - I would not be able to handle all the back and forth you're doing - ugh - that sounds awful!

Currently we only add the Approvers/Approvals ONE software -  the Adobe (ProofHQ) product, and focus on messaging everyone from this platform (not Wrike). The only people in Wrike are the "Doers" (ie the Content Writers, Designers, etc) - it's on them to keep up on connecting the dots with ProofHQ and Wrike's ticket status. I only step in when things are really at risk or in special circumstances. This has helped us a lot too as for me to keep track of Approvals in 2 places (softwares) for all 50 active projects would be a headache and take all my time as a project coordinator! By putting this on the "Doer" to check on the ProofHQ approvals, it has greatly helped us all - it's much easier for each designer to manage 10 or so active project approvals vs me managing 50. 

We also began putting parameters on the Approval process, and added a tiered approach which has done well. 
Stage 1: Creative Team Review (3-4 ppl)
Stage 2: Marketing Team Review (4-6 ppl, most of the Stage 1 folks move to just being Observers, they can comment but aren't making decisions)
Stage 3: Legal/Compliance/Exec Review (2-4 people only, no one from Stage 1 or 2 besides Art Director and Project Coordinator, again they're observers)

Now we've mirrored the Approval Stages in our Wrike Workflow too - and that helps when we're keeping up on everyone and makes it easier to send reminders/track who is pending (see, I'm getting back to your original question, lol).

A few Wrike solutions come to mind:

AUTOMATIONS BASED ON FOLDERS/TAGS/FIELDs

1. Create a Project Coordinator Space that's private and create folders for the outstanding folks. Instead of having to keep up with multiple projects someone is pending, you can set an Automation to Apply to Tasks in "Pending Brenda" Folder AND Assigned to Brenda (and overdue, etc as shown above). No one else can see the "Pending" Folder of Shame besides you or the PCs in the Space
   
   
2. Similarly, create a custom field only select Admins or Project Coordinators can view that tracks who you're pending - and set up automations for this. 

UTILIZE UPDATE VIA EMAIL OPTION IN WRIKE

1. Moving to Email for the updates instead of Wrike, you can even send/schedule emails in Outlook, etc - again to minimize the amount of steps/software clicks the Approvers need to go through - Send an email via Outlook with the Wrike email address included such as: PENDING Brenda, Bob and Brian with a link to the Adobe item. The Wrike ticket will automatically be updated too when you use the email and anyone replys-all with it. Honestly, I would keep everyone on it - maybe some public shame will help a bit :p. I do this now and I move the people who are Observers or who have completed the Approval to the "CC" column and those still needing to complete the task are in the TO line.

TRACK PENDING IN A CUSTOM FIELD

1. Another item we do, an idea I inherited when I joined but I think works well - we have a Custom Field in Wrike that's simply for NOTES - the open field we keep up to date with the status on who is pending approval in our other Adobe/ProofHQ software. Our Directors use this in weekly meetings and it's a good way to just tell the facts when giving status updates: "We're 2 days overdue, PEND approval from Brenda and Bob." To keep it short and sweet we add notes like this: (Today's Date, Initials of Approvers and Original Due Date): Example: 7/18: PEND BB and BC (7.10)
2. We have a special table view set up so it's easy to go down the list and see the status updates, with the Notes column showing when in meetings

AND back to your original question - in the scenario you noted in your OP, here's a few other ideas similar to Mike's:

• SET THE ASSIGNEES AS APPROVERS IN WRIKE: you won't be putting a file in Wrike for them to comment on but you're still adding them as an Approver (such as on a Subtask that only has a link to the Adobe item in it), this can help with you needing to remove them each time too - and allows a little more flexibility for automation 

• CREATE INDIVIDUAL AUTOMATIONS FOR EACH PERSON: I've done this for our team of less than 10 folks or so who aren't as active on Wrike but I want to make sure they get tagged in, I just customized it by selecting the Action to work only if they're tagged, then I have it Comment tagging only the user

• USE A WRIKE INTEGRATION WITH OUTLOOK/GMAIL, etc - this would help with the email option you were hinting at, instead of a comment, it would email them. I actually tested ours with a personal outlook account I had (ie without IT limitations) and it worked - so I could setup a dumby email account just to sync with Wrike and send out Reminder Emails (if our IT team won't let me connect Wrike)

• CREATE AUTOMATIONS TO TAG INDIVIDUAL PEOPLE when status hasn't changed in 1 day (I select our statuses that mirror the Approval Process only, so if it's still showing PENDING I just set it to keep tagging people when it hasn't changed).
  A few things that have worked for me:
  - Including the word "Please" or a ? mark, Wrike said they send email notifications when this is in a mention.
  - Our team uses Microsoft, and I've been including "Add to your To Do List for the day" phrases so it will be filtered into their Outlook/To Do Task List (seems to be working), this would work for any To Do software they have working - any bot or AI catches it since it's spelled out exactly
  -I also started having the comments say "Auto-Bot here...." to keep the 'heat' off of me or a project coordinator - making it seem like it's just a friendly Automation Bot poking them everyday, not me, haha (see image below example)

Sorry for the novel of a post! But I was excited (is that the right word? Misery loves company?) to see someone else battling very similar issues as we do - having to bounce between another Software for Approvals and Wrike. We've been trying to find ways to make it work and continue adapting, so I was excited to share some of the ideas our team has come up with! Take it or leave it, but maybe something will stick! :D  Good luck!