Giving Outlook web a second chance--it's great!

[truemagic]

Recently I bumped into this article on my Google feed (https://www.androidpolice.com/tried-...l-app-android/) so I decided to give Outlook a second chance.

Worth noting I "left" Outlook 10 years ago and my account was around 10+ years old. Surprisingly it's still working and the interface is refreshing and polished unlike umm 10 years ago. I do use Gmail from time-to-time although most of the time I'm sticking with RoundCube (RC) because I'm now fully moved out from all the big tech emails and currently using emails hosted on custom domains. Switching from RC to Gmail back and forth isn't enough to make me impressed and I simply love the simplicity of RC.

Now I'm trying out Outlook (web version) and also mobile app on my Android device. The experience is seamless and I'm even able create up to 10 aliases with Outlook. So I've created one solely for forwarding all my domain emails to this alias and it works flawlessly. After some digging I can also send email from my custom domain using Outlook, it's just so cool. I guess this has been supported for years but rediscovering all these to me feels extra special, having moved away and finding a perfect replacement for Gmail, such as ProtonMail, Tutanota, MailBox, Hey etc.

So far I'm loving the focused email feature on Outlook and at times I thought there're some missing features (like the send from a non-Outlook email) and to my surprise I can find it buried somewhere in the advanced settings. Now it really feels like Outlook is the complete email suite I'm looking for! Most importantly, I can use it for free as it comes with a generous 15Gb.

Screenshot of my clean Outlook interface
https://cloud.tempshr.com/AXR7amYgcV54.png

Last but not least, if you're like me, searching for a perfect replacement for your email, I urge you to give Outlook a try and let me know what you think!

[pjroutledge]

Originally Posted by truemagic

... After some digging I can also send email from my custom domain using Outlook ...

This is intriguing. Can you elaborate, please? Like, how do you set this up?

[chrisretusn]

I used to have three Outlook accounts (hotmail). I deleted one of them now only have two. I had to stop checking my accounts via my email client (Claws Mail on Linux) because setting up OAuth2 is a pain and I needed to create another log in to Azure (Microsoft's cloud service). I now only use the Outlook Android App.

I haven't tried the web interface in a long time, darn near forgot about it.

Just tried it. It nice, about the same as last time I logged in. it's not my main account so it doesn't get much traffic. I was prompt to to enter a code from my cell phone via the Outlook App. before I was logged in.

Here is a screenshot. https://imgur.com/FTiZAgx

I like that background image in your screenshot background.

[truemagic]

Originally Posted by pjroutledge

This is intriguing. Can you elaborate, please? Like, how do you set this up?

1. Follow this link to Add an alias in Outlook
2. Choose "Add an existing email address"
3. Enter domain email "myself@example.com"
4. Click "Add alias"
5. Click on the "Verify" link beside "myself@example.com"

Then check your email (myself@example.com) and click on the verification link. That's it, you can now send from your domain email!

[truemagic]

Originally Posted by chrisretusn

I like that background image in your screenshot background.

Yes the background is nice and I feel the calmness when checking my inbox

In fact it's the one of the default backgrounds provided in the Settings: (Screenshot) https://cloud.tempshr.com/C9VS3AyMwcw0.png

I'm liking Outlook so far, but the main drawback for me right now is that most of the emails go into Junk and I don't think there's a setting to disable or lower spam filtering completely although it's set to "Standard" now, the other is "Strict". Still figuring this one out.

[pjroutledge]

Originally Posted by truemagic

1. Follow this link to Add an alias in Outlook
2. Choose "Add an existing email address"
3. Enter domain email "myself@example.com"
4. Click "Add alias"
5. Click on the "Verify" link beside "myself@example.com"

Then check your email (myself@example.com) and click on the verification link. That's it, you can now send from your domain email!

Hmmm. Didn't work for me.
Online Outlook accepted the alias, and I verified it, but I couldn't send from that email alias. The alias wasn't even listed as an option (ie in the drop down 'From' field).
Still didn't work after logging out and in again.

I tried to send from another (previously verified) alias, and that didn't work either.
The error was 'You don't have permission to send messages from this mailbox.'

I kinda didn't expect it to work. (Also, Outlook's online help says "You may not have permission to send from all the addresses you see in the list.")

truemagic, are you sure there are no other steps?

[truemagic]

Originally Posted by pjroutledge

Hmmm. Didn't work for me.
Online Outlook accepted the alias, and I verified it, but I couldn't send from that email alias. The alias wasn't even listed as an option (ie in the drop down 'From' field).
Still didn't work after logging out and in again.

I tried to send from another (previously verified) alias, and that didn't work either.
The error was 'You don't have permission to send messages from this mailbox.'

I kinda didn't expect it to work. (Also, Outlook's online help says "You may not have permission to send from all the addresses you see in the list.")

truemagic, are you sure there are no other steps?

Are you able to see your verified domain email in Outlook > Settings > Forwarding and IMAP > Email Aliases > Set default From address dropdown?

I've my domain email as default and I sent myself a test email from Outlook (with my domain email in the From: field) and yes it works.

Can you refresh the page maybe?

P.S. Perhaps can anybody else give this a try? I'm sure it works on my side but at this point I'm adding only one domain email, I can try to add a second one to test it out.

[Avion]

Originally Posted by truemagic

Perhaps can anybody else give this a try?

I tested as per instructions here, and I also changed the default address. Yes, it would let me send OK, but the receiving account (Gmail) classed it as spam. Also, Gmail shows the sender as me, with 'via outlook.com' appended. Looking at the Gmail 'Show original' option, shows SPF and DKIM as 'pass' but DMARC shows 'fail'.

Possibly if I removed the DMARC record there may be a different outcome, but I'm not going to do that.

[pjroutledge]

Originally Posted by truemagic

Are you able to see your verified domain email in Outlook > Settings > Forwarding and IMAP > Email Aliases > Set default From address dropdown?

Yes

Originally Posted by truemagic

I've my domain email as default and I sent myself a test email from Outlook (with my domain email in the From: field) and yes it works.

That seems to have been the missing step. I had to set the custom domain alias as the default sending address, then it worked.
I then reset my outlook.com email address as the default to see whether i could still use the custom domain alias, but I couldn't (it disappeared from the drop down list). So it seems that the non-Outlook alias must be set as the default.

Which implies that only one non-Outlook alias would work at any one time.

I also successfully sent an email using the custom alias.

Checking the headers though, I can see that the email has actually been sent from my Outlook address, and has failed DMARC.

So, after verification Outlook lets me use the email address in the From field, but the underlying email still does (as expected) come from the outlook.com domain.

[truemagic]

yes when done this way that the header contains Outlook.com domain is expected as it does not go through proper SMTP server of the originated domain. Also Gmail most likely classify it as spam even if it comes from a proper SMTP server of the domain (yet even Outlook does that). And I think there's no other way around it.

I guess Gmail more or less has this same method of adding your domain email as Send as (send from) address and likely with the same drawback.

[Avion]

Originally Posted by truemagic

I guess Gmail more or less has this same method of adding your domain email as Send as (send from) address and likely with the same drawback.

At least Gmail has the option to add your own domain under the 'Send mail as' option where you can add your own domain SMTP settings. I don't think that Outlook has that same option.

[jdtaylor]

You previously could and I think you still can get them to host it for you at a small cost. Unsure if they still have free hosting option.

[truemagic]

Originally Posted by Avion

At least Gmail has the option to add your own domain under the 'Send mail as' option where you can add your own domain SMTP settings. I don't think that Outlook has that same option.

Indeed GMail takes it one step further by allowing external SMTP sender(s) which is missing from Outlook.

Originally Posted by jdtaylor

You previously could and I think you still can get them to host it for you at a small cost. Unsure if they still have free hosting option.

Do you mean external SMTP support in Outlook? I don't see any option to do that? Or maybe because I'm on the Outlook free and not Outlook365.