Zach I have been using links and host my item on my website. However, funny enough, just yesterday I discovered if I create my automated email from a template that the attachment stays with it. I figured it was a fluke, but it worked.

Hello Zach, hopefully this feature gets rolled out soon. Would hope the attachment feature to be able to automatically refer from the custom field (files), for the purposes of automating emails, with personalized attachments.

Zach please do more than just URLs for attachments. You can actually already do this by adding a Files custom field, adding documents to the task via that custom field, and then using that Files custom field as a function field in the body of the email. This isn't a new thing, you can already do that.

We want the ability to add physical attachments, this is a no brainer for this type of function. Because of the sophistication of phishing, and therefore, spam filters and firewalls, url's in emails can be scrutinized.

Zach I have been attaching links of Google Docs, and they seem to work fine.

I haven't tried, but Clickup URLs might also work.

But many times we need to send the files purely as an attachment and not as a link. (Example: If I have to send an Excel file (not Google Sheet) to all my clients for filling in the information, then I can use the email automation with attachment feature once built, else for now we have to manually send the email to each client.

Doing all the following would be the full solution :-

a) When I need to same attachment to multiple people using automation - The email template creator section should have the facility to add attachments, and then in the action section of automations, when I pick the email template, the file also gets loaded in the action part.

b) When I need different attachment(s) to different people using automation - Let's say I have a list where all my clients are there as a Task, and in all these tasks, a custom field is there where I keep a "monthly reporting pdf" of the respective client. Now, whenever I want to run automation to send the monthly pdf report to all my clients, the automation picks for each client relevant file from the custom field "monthly report" and sends that.