NEW to MAUTIC - Re adding contacts to Segments using Filters

Your software
My Mautic version is: 2.16.1
My PHP version is: 7.3.18

Your problem
My problem is: I have created a Segment Called Job Advert Education, I have set the filter for this segment based on a yes/no field in the contact.


and I have created a campaign based on the segment

and the campaign can be restarted y contacts

The campaign runs, send an email, removes contact from segment and additionally from the campaign(this was not being done automatically) and then sets the Field for the contact to be NO.

The main issue is:
It runs the first time the contact field is set to yes, but if the field is then changed back to yes(it was reset to NO in the campaign) the contact is not readded to the segment.

I have the following CRON jobs, which seem to work but only the first time round:

In essence what I am trying to achieve is:
We have a list of contacts who post new jobs every day, I upload these into Mautic, if they are new contacts it sends an email out reference the job, but if they are already in the system, it updates the job information, and I want it to also email the job information out.
Thus, I thought the easiest way is to use a filter based on a contact field. When I upload the daily jobs, i can set the field to 1 or Yes, the upload will update the job fields and it should add them all to the segment, send the email and then set the field to ) or NO.

Can anyone help me with this?
I came to Mautic from ZOHO, where there was a simple option of do this if field is updated - this seems to be missing in Mautic, so I am trying to find a working solution.

Many thanks for any help.

Best wishes

These errors are showing in the log:

Steps I have tried to fix the problem:

Did you set all the Ceo jobs correctly?

Thanks for he reply @aerendir , I am pretty sure the cron jobs are set correctly as it does run but only the first time of adding the contact to the segment.
Best wishes

So it seems from research that it is to do with updating and changing the bolean field. It does not work. I am not sure Mautic changes the Bolean to NO or 0. If I set this up as a TEXT field it works fine.
I also had to add in two filters, one to check for an email and then check for Y or N, otherwise it wouldn’t work.
Not sure why exactly, but I think what I have now works.