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Outlook.com - Need clarifications : Connected account vs Premium vs Alias

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I need some clarifications between a few things :

For instance :

1- I can set up a personal email address (me@mydomain.com) in the settings to change the from-line of the composer. So I can use that email address to send an email within Outlook.com. And I can have those message sent to that email address forwarded to my Outlook.com account => FREE > That's what I'm doing

2- I can go premium with a custom domain and therefore send and receive messages from and to outlook.com => PAID (granted this includes several users, but this would only concern me)

3- I can use this same personal email address as an alias and, if I'm not mistaken, send messages from that address from Outlook.com => FREE

If someone can clarify all this.

 

Also If I do #1 and #3 could there be some conflicts by having a from-line similar to an alias?

 

 

 

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Solution

1 and 3; With a Connected Account, you are sending via the original SMTP server of the domain so it's less likely that the message will get marked as spam (and also offers the option to collect your mail). If you are sending it as a pure alias, you are using the SMTP servers of Outlook.com so it will more likely get marked as spam (since they don't host your mailing domain), or you are sending it "on behalf of your custom domain" and would actually use your outlook.com address (which is also visible to the recipient) and significantly reduces the risk of having your message marked as spam.

 

2; Discontinued service, although several Premium features are now part of an Office Home / Personal subscription.

 

Note that for proper custom (vanity) domain support, it is currently recommended to get an Office 365 for Business subscription which contains Exchange Online.

Outlook.com Premium is discontinued ? But it’s just been oficially introduced ! Did read about the premium features been added to O365 though
Thanks for your answers Makes sense but seems redundant to me

Outlook.com Premium as a separate product has indeed been discontinued.
See: https://premium.outlook.com/
And: https://blogs.office.com/en-us/2017/10/30/premium-outlook-com-features-now-available-to-office-365-s...

And: https://support.office.com/en-us/article/Outlook-com-Premium-closed-to-new-subscribers-93934667-4db8...

 

The Custom Domain feature (full hosting of the email domain for up to 5 addresses) is no longer being offered via Outlook.com but only via Office 365 for Business (supports much more addresses and features).

 

If you already have an Office 365 subscription or only want to use your mail via browser and/or on mobile mail apps, then Exchange Online is the most affordable solution being offered;

https://products.office.com/en-us/exchange/exchange-online

 

 

Thanks, but my custom domain is a Google Apps account created in 2007, when the service was offered for free.
Other family members have an email address with this domain and use Gmail on a regular basis.
Getting Exchange Online would probably require that I move the whole domain on MS servers, not just one email address, hence my setup consisting in forwarding emails from Gmail to Outlook and choosing the best way to send email from Outlook. I guess I'll stick with a Connected account option

No, you don't have to but it makes the configuration slightly more complex.

 

Using forwarder in Gmail and a (Send Only) Connected Account in Outlook.com is indeed the recommended approach when you already have a custom domain mail hosting provider and don't want to make any additional costs.

If you don't mind, could you tell me more about that configuration you mentioned? I'd love to get full Exchange :p

Do you mean doing the reverse and setting up everything on Exchange and auto forwarding specific email addresses to Gmail ? That would require paying for unused Exchange accounts and opening up brand new Gmail accounts...

It's called Internal Relay;
https://technet.microsoft.com/en-us/library/jj945194

 

In it's simplest form, you'd create a forwarder for your address from your Gmail custom domain to the <tenantname>.onmicrosoft.com address of Office 365 (or another alias), leave the MX records with Gmail and add an additional SPF definition for your domain to validate Office 365 as a sender for your domain or configure a Send Connector so that Office 365 routes all your mail via Gmail.

 

This is basically the same approach as in Outlook.com but then scalable for many more users (as you only need to configure the Send Connector once).

 

You can also do the reverse and make Office 365 the authoritative host for your domain and configure Gmail as a relay. You'd then configure Mail Users in Office 365 to forward the mails (no license is needed for Mail Users). This would make sense when the majority of your accounts is hosted at Office 365.

Great thanks I have to look in to this !
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best response
Solution

1 and 3; With a Connected Account, you are sending via the original SMTP server of the domain so it's less likely that the message will get marked as spam (and also offers the option to collect your mail). If you are sending it as a pure alias, you are using the SMTP servers of Outlook.com so it will more likely get marked as spam (since they don't host your mailing domain), or you are sending it "on behalf of your custom domain" and would actually use your outlook.com address (which is also visible to the recipient) and significantly reduces the risk of having your message marked as spam.

 

2; Discontinued service, although several Premium features are now part of an Office Home / Personal subscription.

 

Note that for proper custom (vanity) domain support, it is currently recommended to get an Office 365 for Business subscription which contains Exchange Online.

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