Have Outlook added to the 'share' menu (under Extensions) in System Preferences. It's time-consuming, and annoying to constantly have to drag files to Outlook — as opposed to being able to sending them via Outlook under the 'share' option. This is a must for businesses, that email a lot of attachments. Thanks.

Messages in Outlook show up in Spotlight searches as Outlook files without content previews. Viewing Outlook messages in Spotlight should be as easy as previewing other file types (including Word and PowerPoint docs).

I had sent a test email from Mailchimp that displayed colors that upon viewing in dark mode had changed from what I had originally selected in my browser. Outlook 16.27 on OS X 10.14.5

It would be nice to be able to create notes within an email for personal use/reminder.

The idea is to have an Icon next to the other Trash, Archive and Flag Icons.
When you click on Notes Icon it pops up and you can make notes or see your notes about that email.

Currently all e-mails which are signed, encrypted or signed+encrypted have the lock symbol in the 'attachement' column. Furthermore when writing a new e-mail and select the option to sign the message a notification bar shows up between the subject and the text showing a lock symbol.
This might be missleading for the user and she might think that the content of a signed e-mail gets encrypted.

When I select an e-mail in my inbox, it opens in the preview pane. As soon as I follow a link in that e-mail, the e-mail isn't highlighted anymore.

I expect the email currently in the preview pane to stay highlighted.

Specs:
Microsoft Outlook for Mac
version 16.28
Office 365 subscription
Dark mode :-)

In the print options it would be very useful to add an option to choose to print attached images with it's email.
Thanks

Currently, every time an email is replied to, a new "You replied to this message..." bar is added to the top of the email. I would request that since the ability to see the conversation history is easily accessible, this be limited to the most recent email.

Search funktions does not work
Search in Outlook does NOT WORK properly - mostly shows NO RESULTS!! Please fix it.

I need some Google calendars, which have personal appointments, to appear in Outlook, so I don't double-book. But I don't need/want gmail from that account to appear in Outlook, too. I can turn off calendars; I should be able to turn off email, too.

I don't need to be pinged for every email in every account. Why not allow per-account notification settings -- including maybe different sounds for each account, or none at all?

In order to print in landscape you need to first go into the page setup menu and change the orientation. If we can make the page setup menu accessible from the print menu, it will make easier for user to navigate.

I have my Outlook configured to mark messages as read when they're selected. Unfortunately Outlook always selects the first message so it can be easily marked as read when it shouldn't be. Apple Mail doesn't have this issue so that's what I'm forced to use :-(

Select multiple emails and right click Attachments>Delete and it deletes all attachments in the selected emails and not just the attachments on the email that was last viewed. It is such a slow process to regain email space on the server.

Add support for digital signature and encryption certificates located on smart cards.

I suggest you add a report phishing button to Outlook for MAC. It provides a more seamless user experience between OS’.

In Windows Outlook you can classify emails from known sources as 'safe' without having to add them to your contacts was you have to in Mac version. I dont want to add Cosco or Honda to my contacts, but I will want to receive mailings, and not have to click on 'Download Pictures' every time.

I remove large file attachments if they're big files, but I'd still like Outlook search to show me the emails those files were attached to. Helpfully Outlook does show you that a file was removed and gives the filename, so the data is still there. Presumably adding this to what the search indexes should therefore be possible?

We would like to have an option to create a rule to delay all outgoing email, like in Outlook for Windows.
Thye idea is to have a small time to cancel the sending if there is something wrong.

You can delay individual messages, but you cannot add a rule to "auto-delay" X time any email you send.