Office/Microsoft 365

Cromulent

Cromulent

Cromulent

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I'm having a hell of a time with something. I've enabled sending from alias addresses using this PowerShell code:

www.derekseaman.com

Microsoft 365: Can now send email as Proxy Address - Derek Seaman's Tech Blog

What has been literally years in the making, Microsoft has just now enabled Microsoft 365 users to send email as a proxy (alias) address. Why is this news? Well Gmail Suite and other business email services have had this feature forever, and some businesses have a hard requirement for such…
www.derekseaman.com www.derekseaman.com

Which I did on my Windows 11 Pro virtual machine. I then went and other things expecting it to take a couple of hours to take effect, but after just checking again, there is no option in Outlook to change the from address that I can see. My main email address has about six alias addresses.

I'm also deciding whether to go with Plan 1 or Plan 2 Visio. I know that the desktop app is Windows only (I use a Mac), but when you go to the comparison site, it doesn't say that all the extra features are app only, or does it add the Plan 2 benefits into the web app as well?
 
If this is Outlook (Windows) then you need to first enable the 'From' field via Options, then 'Show Fields' and then 'From'. Then 'From' field will display a dropdown within a new email that will show the 'Other email address' option where you can specify the sending email address (i don't believe it's a self-populating list).
If it's OWA, then just click on the 'From' field and select 'Other email address' etc.

I would argue for shared mailboxes for each "additional" address but appreciate that can also be a faff.
 
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visibleman said:
If this is Outlook (Windows) then you need to first enable the 'From' field via Options, then 'Show Fields' and then 'From'. Then 'From' field will display a dropdown within a new email that will show the 'Other email address' option where you can specify the sending email address (i don't believe it's a self-populating list).
If it's OWA, then just click on the 'From' field and select 'Other email address' etc.

I would argue for shared mailboxes for each "additional" address but appreciate that can also be a faff.
Click to expand...
I've tried it with Outlook on the Mac and don't see a "From" button. I looked through all the settings and couldn't see an option for "From" addresses. I tried it on OWA and do see a "From" button, but it doesn't show all the email aliases, which seems a bit weird. I'll have a look at Outlook on Windows 11.

If I were to use shared mailboxes, what would the requirements be to move them to a new user with a new 365 account? I'm mainly planning on using the aliases to see if a plan will work out before I start spending money on extra accounts.

Thank you.
 
Cromulent said:
I've tried it with Outlook on the Mac and don't see a "From" button. I looked through all the settings and couldn't see an option for "From" addresses. I tried it on OWA and do see a "From" button, but it doesn't show all the email aliases, which seems a bit weird. I'll have a look at Outlook on Windows 11.
Click to expand...
Outlook for Mac doesn't currently support it, it's on the roadmap. Closest (current) option would be to either use multiple (licenced) mailboxes/users or shared mailboxes; once setup, the 'From' field is displayed/becomes a dropdown.

OWA doesn't always populate fully and you tend to have to manually type the address in, similarly with Outlook Window (iirc; been a while since i've used it).
Worth checking the aliases on your account/mailbox under Admin Center or EAC and making sure they're all there and setup correctly though.

Cromulent said:
If I were to use shared mailboxes, what would the requirements be to move them to a new user with a new 365 account? I'm mainly planning on using the aliases to see if a plan will work out before I start spending money on extra accounts.
Click to expand...
You can convert between regular and shared (and vice versa) within EAC (Exchange Admin Center) and the only requirement is licencing.
Once you convert a shared mailboxes to a "regular" mailbox (rather a user account with a mailbox attached), you have to assign it an appropriate Exchange licence ('Exchange Online', 'Business *', 'E*' etc). When converting "regular" mailboxes to shared, the assigned users need the appropriate licencing.

Alternatively you can also use Groups and allow assigned users to 'Send mail on behalf of' but, it flags in emails.

If you're dealing with Mac's and Office/MS365 then the Macadmins Slack is worth a visit as a good handful of MS Engineers and Leads hang out on it and it's usually the quickest way to get information and/or help, especially as the usual MS support channels can be painful at times.
 
visibleman said:
Outlook for Mac doesn't currently support it, it's on the roadmap. Closest (current) option would be to either use multiple (licenced) mailboxes/users or shared mailboxes; once setup, the 'From' field is displayed/becomes a dropdown.

OWA doesn't always populate fully and you tend to have to manually type the address in, similarly with Outlook Window (iirc; been a while since i've used it).
Worth checking the aliases on your account/mailbox under Admin Center or EAC and making sure they're all there and setup correctly though.


You can convert between regular and shared (and vice versa) within EAC (Exchange Admin Center) and the only requirement is licencing.
Once you convert a shared mailboxes to a "regular" mailbox (rather a user account with a mailbox attached), you have to assign it an appropriate Exchange licence ('Exchange Online', 'Business *', 'E*' etc). When converting "regular" mailboxes to shared, the assigned users need the appropriate licencing.

Alternatively you can also use Groups and allow assigned users to 'Send mail on behalf of' but, it flags in emails.

If you're dealing with Mac's and Office/MS365 then the Macadmins Slack is worth a visit as a good handful of MS Engineers and Leads hang out on it and it's usually the quickest way to get information and/or help, especially as the usual MS support channels can be painful at times.
Click to expand...
Thank you very much for your help. That was very useful!
 
visibleman said:
@Cromulent - Yet to test this but thought i'd let you know, the latest 16.73 Outlook (/Office) update supposedly includes support for aliases (Changelog).
Click to expand...
Thank you. I've had a quick play around with it. I can send emails from my shared mailbox but not from my aliases. I've checked the version of Outlook I am using, and it matches, but I'm unsure what to do. Selecting other email addresses doesn't show any of the aliases.
 
@Cromulent - Just to double check, have you got alias sending enabled?
You can check via EAC (Exchange Admin Center) > Settings > Mail Flow, and then under 'General', make sure 'Turn on sending from aliases' is enabled. If not, enable it, click Save and give it 5/10 minutes.
 
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visibleman said:
@Cromulent - Just to double check, have you got alias sending enabled?
You can check via EAC (Exchange Admin Center) > Settings > Mail Flow, and then under 'General', make sure 'Turn on sending from aliases' is enabled. If not, enable it, click Save and give it 5/10 minutes.
Click to expand...
Is that the PowerShell code in the link of my first post or something extra? I'll have a look.
 
visibleman said:
IIRC, SendFromAliasEnabled does the same but it's worth checking within EAC just to make sure it's actually enabled.
Click to expand...
Hmm. I had a hunt around in EAC and didn't see a general option in mail flow. I searched for alias but nothing came up. I'm using the new EAC admin panel but even after switching back to the legacy EAC I still couldn't find anything.
 
Cromulent said:
Hmm. I had a hunt around in EAC and didn't see a general option in mail flow. I searched for alias but nothing came up. I'm using the new EAC admin panel but even after switching back to the legacy EAC I still couldn't find anything.
Click to expand...
Try https://admin.exchange.microsoft.com/#/settings for EAC Settings. Then click 'Mail flow' for the 'slide-in' menu, then under the 'General' heading (should have made that clearer), you have the option 'Turn on sending from aliases'...

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Cromulent said:
Thank you. I did that, and it was already ticked, which is a bit weird. Maybe I should speak to 365 support.
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The only thought would to be disable it, leave it a few hours and then re-enable just on the off chance the PS config bodged somewhere.
But otherwise, MS support is your next port of call as it could be something with the tennant that's at fault.
 
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