Online email, should I use Gmail or Outlook.com?

[csdude55]

For several years I've been using Gmail as my primary email, with my server redirecting [e-mail] to the Gmail and then using my server's SMTP for the outgoing. So the end users email [e-mail] and when I reply they see [e-mail], but I'm able to see the email at Gmail.com on my computers, phone, etc.

I also IMAP the Gmail to my Outlook 365, mainly so that I can automatically archive emails from Gmail to a local .PST file and save room on my Google account. I don't pay for the Google account so I have 15G, and my email archive is a little over 12G by itself!

(Note that I pay for 365 instead of Google because my girlfriend really likes using Outlook on her computer and occasionally uses some of the other Office programs. I also have 1TB of OneDrive cloud storage with it, so that helps when we're sharing files.)

But my main computer gave up the ghost a few weeks ago.

I was able to save the .PST files so I didn't lose my archives emails, but I'm going to have to start over on creating the accounts in Outlook, all of the archive rules and settings, etc :-(

That's when I saw... Outlook.com can do the same thing as Outlook, and as a 365 subscriber it comes with 50G of storage!

So now I'm debating on 3 options:

1. Go back to the way it was before, using the downloaded Outlook to archive everything as needed

2. Upload all of the local stuff to Outlook.com and keep it online instead of locally (advantage is that if I have a computer crash then it will be protected; disadvantage is that I have to keep paying for 365 indefinitely)

3. Abandon Gmail entirely, and set up Outlook.com to send through my server the way that Gmail was. Then I can forget about archiving altogether

Which would you do? I'm leaning towards the third option, but since I've never used Outlook.com I'm a little nervous about going all in and then regretting it for some reason.

Are there any advantages / disadvantages to using Outlook.com over Gmail.com?

[tangor]

Hard to say. Usually "least pain for greatest gain" would be step one. You are already familiar with both ... so which one would you LEAN TOWARD if you could only use ONE?

I'm not much help since I run my own mail server for all the obvious reasons. :)

[csdude55]

I'm actually not familiar with Outlook.com at all, today was my first time looking at it!

At this point, though, I'm not seeing a way to change the SMTP server, the default email, or my name. I might do a support chat session tomorrow, but if I can't change those then it's useless :-(

I had a VERY weird experience with Outlook.com, too.

I tried sending myself an email, and the default From is my Gmail address that I'm importing. I clicked on the From button and it let me change it to... anything! I changed it to [e-mail] and sent myself an email, and it went through! No errors, no SPF or DMARC catch, nothing. And when it arrived to my Gmail, it looked to me like it had originated from Gmail!

That clearly should NOT have worked, but it did.

[csdude55]

After some chatting with a Microsoft agent, I don't think that Outlook.com is going to work at all. He didn't clearly answer my question of how to change the SMTP settings, my default reply email, or name, which makes me think that it can't be done.

The format would have been fine, and the additional storage would have been great! But I don't think that their format is really intended for businesses.

[Dimitri]

Why not run your own mail server?

[csdude55]

I did that for a long time, but I was having an issue with my emails going to recipients spam folders (especially when the recipient is Gmail) so I thought I'd try to funnel them through Gmail instead. I don't know if it REALLY helped, but I also liked not filling up my server's drive with email. Before COVID I had 10 people using email, and all of them being IMAPed through my server would have filled it up! LOL

I gave up on Outlook.com, though, and ended up paying $20 /year for Google One to have 100G of storage. I'm still moving emails to Gmail from Outlook, but I look forward to just eliminating Outlook entirely! I've had nothing but problems with it since then beginning.

[Kendo]

I was having an issue with my emails going to recipients spam folders (especially when the recipient is Gmail)

It doesn't make much difference. Gmail has silly rules and almost all commercial looking email goes into the spam folder. Besides most spammers use a gmail account anyway.

[Brett_Tabke]

> Why not run your own mail server?

Because spam is unforgiving and you will suffer greatly under it's load. I can't imagine trying to run my own email server again.

We use office365 with outlook. I am not fond of how big-n-beefy the whole system is, but it seems to work.

[Future]

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