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Here is what I have:

  • 2 school email accounts (all Exchange)
  • 1 school email account hosted via live@edu's version of exchange

    Exchange, but with some identity quirks because the account is also a "live id"

  • 1 Hotmail account I have used for ages (and will continue to use) primarily this email is used for personal and professional correspondance (anything not school or work related)
  • 1 Work account (Exchange with all the bells and whistles)
I also have the following, less important emails:

  • about.me account (what the heck, right? giving aol another chance)
  • a besmattering of other old email accounts that a few people from the dark ages occasionally email me from. Some of these I could live with just forwarding the mail and responding from a different account.

Here are the devices and platforms I use every day:

  • Windows Phone
  • Windows 8 Tablet (the metro mail app primarily, although I have outlook installed)
  • iPad
  • Macbook Air

I recently signed up for a personal Office 365 Account, and I love the concept of it, however it kind of blows. Here's why:

  • The connected accounts are all only checked every half an hour unless I'm signed in to OWA (the exception being by Hotmail and live@edu account since Microsoft on the backend implemented their own DeltaSync)
  • Sending emails via a "connected account" is only possible through either OWA, or by configuring each account on each device, and making sure you remember to "reply" from the right email address. Doing this is a hassle since each device/machine gets its image rebuilt every month or so. Additionally, WP7 phones do not support the "send as" feature, but instead allow you to "link" your email accounts together, which means having all your accounts on your phone, and having Office 365 that's connected to all of them makes your inbox look messy, and horrible.
  • Connected accounts that are not exchange or IMAP accounts (read: hotmail) will only be able to retrieve email from the root "inbox" folder. Thus, to use Office 365 effectively, you need to delete all your rules from Hotmail (exporting such rules is not supported)

The feature to "send on behalf of" another account (provided by Hotmail, Google, Exchange) is in my opinion unprofessional an discourteous. I don't really look down on anyone who uses it (would be silly to), but I have a strong conviction that when I'm corresponding with fellow classmates, they only need to know about my school email. Likewise with personal / professional correspondance where I want the identity of the sender (me) to be crystal clear. Obviously this feature is completely inappropriate for work use.

So... what do the best and brightest emailers out there recommend? I want to have one access point for all my email, have that access point be completely transparent to the people I correspond with, and I want to be able to use the configuration with minimal set up on all my devices. I'm happy to put time and effort into configuration on the server side, so long as it translates to the mail clients I use.

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"send on behalf of" can be bypassed if you configure Gmail to use your school's SMTP servers for sending from that particular address. – grawity May 15 '12 at 20:16
That's good to know. I have heard that often this sort of thing results in your emails getting filtered as "junk" email by a lot of email clients. Is that at all true? Or is that strictly for spoofing situations where the "From" header is actually altered? – Paul Hazen May 15 '12 at 20:50
It is true that messages claiming to be "From:" domain A but actually sent by domain B's servers can be filtered. The "on behalf of" part is added specifically to avoid this, by intentionally revealing the actual message sender in the "Sender:" header. When configuring Gmail to use the school's SMTP servers, however, this becomes unnecessary, since the messages with "From: @school.edu" will actually be sent via school.edu's servers, containing no references to Gmail. – grawity May 15 '12 at 21:52
Okay, had a suspicion that was the case. Looks like Google also supports such support for connecting Hotmail email, which is great. Gah... Might have to use them. I have all my proverbial service eggs in one basket (Microsoft) which is so nice, hate having to resort to adding another service provider for something like this. – Paul Hazen May 15 '12 at 22:57

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