Gmail or iCloud Mail?

[Rigby]

If have now tested Outlook.com for a few days and I will switch everything over. It works really well and has a nice feature set:

- Full EAS support, i.e. push email, contacts and calendar
- IMAP support for Mac Mail and other non-Outlook clients
- Very nice, clean web interface
- Up to 10 email aliases (i.e. no need to set up multiple accounts as in Gmail), and "+" aliases
- Good filter rule system
- 2-factor authentication using offline code generators (e.g. Google Authenticator); I'm at a loss why Apple still doesn't have that on icloud.com
- You can configure your own "From" address for outgoing mails, i.e. you can continue to use a non-Outlook address if you want to
- Doesn't scan your emails for ad profiling purposes

The first Microsoft service I really like.

 

[dmk1974]

- You can configure your own "From" address for outgoing mails, i.e. you can continue to use a non-Outlook address if you want to

Can you also configure your iPhone to do this from the native iOS Mail app? Or only from the web interface?

 

[eawmp1]

Can you also configure your iPhone to do this from the native iOS Mail app? Or only from the web interface?

From the phone

 

[dmk1974]

From the phone

Can you step me through how? When I set up Outlook mail on my iPhone, I don't see anywhere to edit that. It always sends from my xxx@outlook.com address.

 

[Rigby]

Can you also configure your iPhone to do this from the native iOS Mail app? Or only from the web interface?

If you use EAS, it can AFAIK only be done from the web interface. Whatever "From" address you configure, will be used regardless of the settings of the mail client if you use Outlook for sending. However, you could set up a separate SMTP server for the other mail service; then you get a choice of the mail address when you compose the mail on iPhone.

 

[dmk1974]

If you use EAS, it can AFAIK only be done from the web interface. Whatever "From" address you configure, will be used regardless of the settings of the mail client if you use Outlook for sending. However, you could set up a separate SMTP server for the other mail service; then you get a choice of the mail address when you compose the mail on iPhone.

I set it up as EAS on my iPhone so I get the push email received. So I would have to set up a second email account that has the SMTP enabled for sending, and then every time I reply to an email received in the Outlook EAS account, I'd have to toggle the From field to my alias? If so, that's a possibility, but kinda a pain in case I forget to toggle it.

 

[Rigby]

I set it up as EAS on my iPhone so I get the push email received. So I would have to set up a second email account that has the SMTP enabled for sending, and then every time I reply to an email received in the Outlook EAS account, I'd have to toggle the From field to my alias?

What are you trying to achieve? If you want do use the other address every time, just configure it in Outlook.com.

 

[dmk1974]

What are you trying to achieve? If you want do use the other address every time, just configure it in Outlook.com.

In Outlook.com, I had no problem configuring it so when I send an email, it goes to the recipients from my xxx@alias.com account (even though logged into my xxx@outlook.com account). But from the iPhone, set up as EAS, it always is seen by the recipients as from the xxx@outlook.com address.

 

[blhoward2]

Can you step me through how? When I set up Outlook mail on my iPhone, I don't see anywhere to edit that. It always sends from my xxx@outlook.com address.

Whatever you set your Reply-To address for on the website is what your phone's email will come from.

 

[dmk1974]

Whatever you set your Reply-To address for on the website is what your phone's email will come from.

Well, no dice for me for some reason. Again, works fine from the outlook.com web browser interface. Not from the iPhone.

 

[Rigby]

In Outlook.com, I had no problem configuring it so when I send an email, it goes to the recipients from my xxx@alias.com account (even though logged into my xxx@outlook.com account). But from the iPhone, set up as EAS, it always is seen by the recipients as from the xxx@outlook.com address.

Once you have linked an external mail account (send-receive or send-only), you can pick the default From address under "Inbox>Options>Your email accounts". That address will be used for all outgoing mail sent from mail clients like iOS Mail. Do not use Reply-To.

 

[dmk1974]

Once you have linked an external mail account (send-receive or send-only), you can pick the default From address under "Inbox>Options>Your email accounts". That address will be used for all outgoing mail sent from mail clients like iOS Mail. Do not use Reply-To.

Thank you! Linking the account worked from the iPhone and can send from my alias.

So I am now receiving push e-mail on my iPhone, sending from my alias. Emails get delivered to both gmail and outlook. When I read in outlook, it doesn't mark as read in gmail, but I can go in later to mark as read (unless there's a way to set that automatically). It is nice that the sent messages show in both outlook and gmail.

 

[bluebit]

- 2-factor authentication using offline code generators (e.g. Google Authenticator); I'm at a loss why Apple still doesn't have that on icloud.com

I'd like to get away from GMail, but the lack of a true 2-factor auth is stopping me from moving to iCloud. Outlook.com is definitely an option, but I'd rather just use what Apple gives me.

 

[APhillyApple]

I use iCloud, I closed Gmail after this became the Apple standard.

 

[Rigby]

I'd like to get away from GMail, but the lack of a true 2-factor auth is stopping me from moving to iCloud. Outlook.com is definitely an option, but I'd rather just use what Apple gives me.

I understand. I think iCloud security is terrible by modern standards. Considering how much damage can be done just via the icloud.com web page (not just reading all your info, but also tracking and remote wiping your devices), it is really irresponsible to use just a simple password to protect the account. Especially since it is not very practical to use a long, complex password, since you have to type it quite often and on mobile devices ...

 

[dmk1974]

If have now tested Outlook.com for a few days and I will switch everything over. It works really well and has a nice feature set:

- Full EAS support, i.e. push email, contacts and calendar
- IMAP support for Mac Mail and other non-Outlook clients
- Very nice, clean web interface
- Up to 10 email aliases (i.e. no need to set up multiple accounts as in Gmail), and "+" aliases
- Good filter rule system
- 2-factor authentication using offline code generators (e.g. Google Authenticator); I'm at a loss why Apple still doesn't have that on icloud.com
- You can configure your own "From" address for outgoing mails, i.e. you can continue to use a non-Outlook address if you want to
- Doesn't scan your emails for ad profiling purposes

The first Microsoft service I really like.

Did you continue using Outlook now about a week later? If so, still like it?

 

[whsbuss]

If have now tested Outlook.com for a few days and I will switch everything over. It works really well and has a nice feature set:

- Full EAS support, i.e. push email, contacts and calendar
- IMAP support for Mac Mail and other non-Outlook clients
- Very nice, clean web interface
- Up to 10 email aliases (i.e. no need to set up multiple accounts as in Gmail), and "+" aliases
- Good filter rule system
- 2-factor authentication using offline code generators (e.g. Google Authenticator); I'm at a loss why Apple still doesn't have that on icloud.com
- You can configure your own "From" address for outgoing mails, i.e. you can continue to use a non-Outlook address if you want to
- Doesn't scan your emails for ad profiling purposes

The first Microsoft service I really like.

Such praise..... well I can tell you Mac mail on mountain lion does not work properly with Outlook.com IMAP. Deleting or moving messages in the inbox on mac mail does not sync with iOS or web interface.

 

[Rigby]

Such praise..... well I can tell you Mac mail on mountain lion does not work properly with Outlook.com IMAP. Deleting or moving messages in the inbox on mac mail does not sync with iOS or web interface.

Well, I can tell you it works just fine with Mac Mail. I have it right in front of me. Probably you set up the account wrong. You have to "trick" Mail to set it up as IMAP, since the setup wizard wrongly assumes that Outlook.com supports only POP. See here for some instructions.

----------

Did you continue using Outlook now about a week later? If so, still like it?

Yep. I moved my mail archive over and it's now my primary mail account. No problems so far.

 

[whsbuss]

Well, I can tell you it works just fine with Mac Mail. I have it right in front of me. Probably you set up the account wrong. You have to "trick" Mail to set it up as IMAP, since the setup wizard wrongly assumes that Outlook.com supports only POP. See here for some instructions.

Sorry but it does not work for me. Yes indeed IMAP is setup correctly. There are many users on Apple's forum having tons of issues. Glad it works for you. I suspect the problems lies with Outlook.com using EAS for mobile and IMAP for remote mail client. Do a google search for "Outlook.com IMAP issues" and you will see. Try again.... setup outlook.com on your iPhone then send a message. In mac mail, read then delete it. Then see on your iPhone if it gets deleted or just sits in your inbox.

 

[Rigby]

Sorry but it does not work for me. Yes indeed IMAP is setup correctly. There are many users on Apple's forum having tons of issues. Glad it works for you. I suspect the problems lies with Outlook.com using EAS for mobile and IMAP for remote mail client.

I think most of these cases are improper mail client configurations. Make sure that:

- You tell Mail to use the same folder for deleted messages ("use this mailbox for" menu) that the web interface (and EAS clients) use
- You disable creating a copy of sent mails in Mail; the Outlook.com SMTP server does this automatically (for consistency again make sure that Mail uses the same folder)
- You are aware that Mac Mail does not do an IMAP Expunge before exiting the client, i.e. deletes do not sync with the server until you close Mail

setup outlook.com on your iPhone then send a message. In mac mail, read then delete it. Then see on your iPhone if it gets deleted or just sits in your inbox.

Works fine here (provided that you exit Mail as mentioned above or do an explicit expunge in Thunderbird). I use Outlook's IMAP service with Mac Mail and with Thunderbird on a PC and have no such problems with either of them.

 

[whsbuss]

I think most of these cases are improper mail client configurations. Make sure that:

- You tell Mail to use the same folder for deleted messages ("use this mailbox for" menu) that the web interface (and EAS clients) use
- You disable creating a copy of sent mails in Mail; the Outlook.com SMTP server does this automatically (for consistency again make sure that Mail uses the same folder)
- You are aware that Mac Mail does not do an IMAP Expunge before exiting the client, i.e. deletes do not sync with the server until you close Mail
Works fine here (provided that you exit Mail as mentioned above or do an explicit expunge in Thunderbird). I use Outlook's IMAP service with Mac Mail and with Thunderbird on a PC and have no such problems with either of them.

Okay let's discuss.

I have setup IMAP in mac mail numerous times:

- I set the Deleted folder for "use this mailbox for trash" which then changes that folder to "Deleted Messages" and under Trash the Outlook trash gets set.
- I have also set the Sent folder for "use this mailbox for sent mail" so the web interface sees emails sent from mac mail.

As far a IMAP expunge I have tried both quitting mac mail and sync'ing via the mac mail menu for outlook and it still exhibits this problem. None of my iOS devices or the web interface for outlook.com shows deleted emails.

 

[whsbuss]

Well the only way to sync the deleted messages for outlook (besides force quitting mail) is to select Mailbox->Erase Deleted Items->Outlook from the mail menu.

Not sure why this is the case for Outlook.com where my AOL.com IMAP works fine.

 

[Rigby]

Well the only way to sync the deleted messages for outlook (besides force quitting mail) is to select Mailbox->Erase Deleted Items->Outlook from the mail menu.

Not sure why this is the case for Outlook.com where my AOL.com IMAP works fine.

Never used AOL, but perhaps it behaves similar to Gmail, which has an "auto-expunge" option under the IMAP settings. Basically the server will automatically execute an expunge if you mark an email as deleted. But normally the client is supposed to do that.

 

[jccfork]

I'm in the same juncture.

All my devices are from Apple and I want a seamless experience, so I find annoying the need of a third app (Gmail app) just for the damn push.
Indeed considering iCloud and Outlook... will switch to any of both soon I think.

As casual mail user (the most I configure is just some folders for keep everything in order), I think it won't be a problem.

 

[Bear]

I've had a gmail account since early on that I've played with. I've also had a .mac account for a long time.

I prefer iCloud. Gmail usese a non-standard imap implementation that can cause issues with imap clients - even ones that know about gmail's quirks. Also, I don't trust google to not change their imap implementation on a whim breaking the imap clients that knew about the quirks.

I've had no problems using .mac/mobileme/icloud email with other imap clients.

And finally, I have to use the web interface for gmail every so often to make sure mail I had deleted is really deleted.

In short, go with iCloud Mail and not gmail. And one thing to think about - with Apple you are the customer and with Google you are the product they are selling.