How to configure “Send As” email in Office 365 Account?

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Himesh SHAH

Outlook version
Outlook 2013 32 bit
Email Account (as MS Exchange)
I have 2 Domains which are used as under:
Domain ‘A’ : Hosted on Gmail & is used for regular communication.
Domain ‘B’ : Hosted on Office 365 for Cloud Computing / Back Up / Syncing across all devices.

Both Domains / Email address are configured in Microsoft Outlook 2013. I want to send email from Domain ‘B’ thru Microsoft Outlook 2013 OR OWA but when the receiver press ‘Reply’ button, he / she should get my email address of Domain ‘A’ in their ‘To’ Address Bar of their email program or Web / Browser based Email.

Appreciate all the assistance.
So you want replies going back to the gmail account? Or just send as the gmail account using office 365? If you add the gmail address as a contact in the gal and give yourself send as permission to it, it might work (I'm testing it now but need to wait about 30 minutes for permissions to propagate.) I suspect it will work like a connected account and send on behalf of. See for the contact method.

You can add the gmail account to your mailbox as a connected account - you can select it in outlook and send on behalf of it.

If you own domain A, you can move it to office365 - there is no fee for additional domains.[DOUBLEPOST=1408638806,1408637941][/DOUBLEPOST]oooh... the contact worked. one issue - SPF. if you own the domain, create an spf record so office365 is an allowed sender.

this is the result when sent to an account- my office 365 address is not in the header, so no sent on behalf.

Authentication-Results:; spf=softfail (sender IP is; identity alignment result is pass and alignment mode is relaxed); dkim=none (identity alignment result is pass and alignment mode is relaxed); x-hmca=fail
Thanks for your replies & sorry for confusing you.

I have hosted Domain ‘A’ on Gmail which is used by my Company for regular email communication. All emails from my Company including me are sent & received from / on this Domain ‘A’.

I have opted for Cloud Storage by Opting Office 365 Subscription. For this I have registered another Domain ‘B’.
When I receive email from my regular Domain i.e. ‘A’, the emails are moved in particular Folder (Z) of my Microsoft Outlook 2013 in my Desktop Microsoft Outlook which is uploaded in Folder ‘Z’ in OWA which is downloaded in Folder ‘Z’ of Microsoft Outlook 2010 in my Laptop. In the same way, when I send email from Domain ‘A’ from my Desktop Outlook 2013, they are moved to ‘Sent Item’ which is uploaded to ‘Sent Item’ in OWA which is downloaded in ‘Sent Item’ of my Laptop. In the same way when I send or receive emails from my Laptop, they are Synced with OWA which are further Synced with my Desktop Microsoft Outlook.
This Syncing is done with my Office 365 subscription.

Since I have budgetary limitation, I cannot take all my staff on Office 365 Subscription. I needed Syncing program which automatically Syncs Email, Contacts & Calendars with both my devices i.e. Desktop & Laptop.

Now I want to opt for Windows phone & since there is no facility of Microsoft Outlook in this System, I cannot replicate the above scenario. If I can send Email from my Domain ‘B’ when I opt for Windows phone & if the recipient replies, I want to get my email to Domain ‘A’ email address. This is how I can keep all my Devices i.e. Windows Phone, Desktop & Laptop always Synced with each other. This is the reason I want to have facility of having email “Send As” Domain ‘A’ email address from my Domain ‘B’.

I hope I am not further confusing you!

PS : Ms. Diane Poremsky : I sincerely appreciate you for giving guidance on various forums. I was able to sort many problems related to Microsoft Outlook by reading your posts. God Bless you & keep up the good work.
The phone has limited options and is definitely the problem area since you can't send as other addresses. Even setting the account up on the phone as imap won't help - you can't set a different reply address. One option is add the google account to the phone as an imap account and use it when you need to send mail from the phone.
Is it possible to have “Connected Account” in OWA / O365 of my Domain ‘A’ & then use “Send As”?
Yes, when you use a connected account, you can send from it using outlook BUT the messages are sent on behalf of (or were, last time I tested it).

I don't know how it would work if do the contact with send as permission as mentioned above - or if the connected account with override the contact.
I got following issues & request your further guidance / assistance:

Issue #1 :
A secured connection couldn't be established to this account. Not all providers offer secured connections. Would you like to try an unsecured connection instead?
** When I opted for unsecured connection Issue #2 came up.

Issue #2 :
Outlook Web App couldn't connect to the server for your other account. Please click the Back button and make sure that you entered your email address and password correctly.
If they're correct, make sure POP or IMAP access is enabled for your other account. If you don't know how to find that setting, read this.
If the problem continues, you can enter POP or IMAP connection settings for your other account.
** When I entered POP details, Issue #3 came up.

Issue #3 :
It looks like it's not possible to leave messages on the server for your connected account.
(If you select this check box, email from the account you're connecting to will be pulled in to your Outlook Web App Inbox and also remain in your other account. If you don't select the check box, email will be deleted from your other account after it's pulled in to Outlook Web App.)
** What will happen if I un-tick the Box? Does this means that there will be NO email left on my Gmail Account as these will be pulled to O365 Account?
#2 means office365 can't connect to the mail server. When i tested a connected account, it lost the connection every few weeks - setting the other account to forward worked better for me.

#3 When the box is selected, mail is left on the other server. When it's not ticked, mail is deleted from the other server as office365 grabs it. This is similar to Outlook's POP3 options to leave mail on the server.

Gmail has 'leave on server' settings of it's own which override the Office365 settings. So ticking/not ticking that box may have no affect on gmail.
I did “Connected Account” Set Up & it is working as I want to!
I did test message to my other email address & when I replied to that message it came in the same Domain where I want my reply to be received.
Now the only concern is that the connectivity between OWA / O365 & Gmail must work seamlessly. Not like my LinkedIn Account which is frequently disconnected. I have to remove this Account & then again connect it to get updated contacts of LinkedIn in Microsoft Outlook.

One more question!
After doing setup of “Connected Account” (of Domain ‘A’) in OWA / O365, will “Send As” work on Windows Phone, Blackberry OS10 Phone and Android OS Phone & Tab?

Thanks & appreciate for your continuous assistance.
AFAIK, send as is not supported on the devices, but its been awhile since i last tested it with an ipad. The devices all use EAS to sync, so it should work the same on all.
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