I need a way to send automatic replies to the same sender multiple times

Thank you for responding.

I removed the rule and started it over, exactly as you have it written.

What is happening now is that it only applies the rule when i open outlook, not while its open. if i try to run the rule manually with emails i received after outlook was opened and the inbox is already updated, it does not run despite being manually ran.

Dear PTR Scheduling

Thanks a lot for your feedback and patience!

Based on your further description, I did a similiar test in my classic outlook desktop client, please kindly check following screesnhots. And it works well now, but given that I just created this rule, so I can't revert your issue, I need to ask you for confirmation that your rule you mentioned sometimes works and sometimes doesn't? This is very strange, under normal circumstances, once the rule is made, it will always run, so first I would like to ask you to delete this rule and restart your Outlook client, and check if your classic Outlook client has been updated to the latest version, if not, please update and re-create this rule to check the result, thank you. For our reference: Install the latest applicable updates for Outlook - Outlook | Microsoft Learn

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Sincerely hope that your problem will be solved as soon as possible! Wish you have a wonderful day!

Sincerely

Kerry Chen | Community Moderator

I understand it cannot be done with out of office, but i am trying to use a rule to make this happen. so currently I have a rule that applies to all incoming messages, and is supposed to reply with an email from a template. it seems to work only sporadically. is there a way to force the rule to run at set times?

Dear PTR Scheduling

Good day! Thank you for posting to the Microsoft Community. We are happy to help you!

First of all, we regret for the inconvenience caused to your work. Based on your description, I have a general understanding of your question, actually it’s not feasible to set up an auto reply on the Office 365 to every incoming message with an automatic replies message on the server side/Office 365. When the Automatic reply *(Out of Office)*is enabled, only one reply is sent to each sender, even if you receive multiple messages from that person.

We understand your feelings, but unfortunately, our forum does not have permission to help you change, because the default feature changes of the product are decided by the development team and the design team of the product. And about your suggestions, I also believe that this is the voice of many users, everyone is anxiously looking forward to early improvement, in order not to waste more time and better help you, I strongly recommend that you submit your valuable suggestions to outlook feedback so that relevant technical developers and designers can see your valuable suggestions. Please believe that the relevant departments of Microsoft will strive to improve themselves after seeing your valuable suggestions, and your valuable opinions will also help more users and make the work more efficient. Thank you in advance for your contribution!

And about how to give feedback, please kindly refer to How do I give feedback on Microsoft 365? - Microsoft Support

In the meantime, you can also use this link to see if the feature you want to implement is already being developed by Microsoft, please also kindly click on it to get the development progress: Microsoft 365 roadmap

Thank you in advance for your understanding! Your patience and cooperation will be greatly appreciated. I hope all the best!

Sincerely

Kerry Chen | Community Moderator