Can't send email through connected account (outlook.live.com) - goes to Drafts folder

[Thomas Inman]

Hi Diane,

I bought a new computer that came with Office 365 Home, and after going to office.com/setup per the instructions on the product key card that came with it, I had to create an account. I entered user1@Outlook.com, and a new account was created so that I could access the web console to install the Office applications on my computer.

I then went to Outlook.com, signed in with user1@outlook.com, and proceeded to 'connected accounts' where I added my Comcast email account. The status showed 'update in progress' as it retrieved all my Comcast email and placed it into the existing Inbox and sub-folders (instead of a separate folder). Status changed to 'up to date', and new emails show up in the Inbox.

I changed the 'From address' to my Comcast email, and also set it as the primary alias to use in the 'Email Alias' section just below that. Once I selected Comcast as the primary alias, I removed the user1@outlook.com alias listed there, and thought everything was all set perfectly until I tried to send an email. When I try to send an email now, it goes into the Drafts folder. When I go into Drafts and try to resend the message, I get an error message, "couldn't send the following message". Repeated attempts to send messages stuffed in the Drafts folder result in the same error message. Note that with this configuration, I am able to sign into outlook.live.com with my Comcast email address as the username, and those credentials are what is shown in the details of the Comcast account under 'Connected Accounts.'

I got on a live chat with Microsoft Answer Desk, gave her remote control of my screen, and after watching her go through the same steps I took in connecting my Comcast account, she referred the case to tier 2 support, who is supposed to call me on the phone tomorrow to help. Not going to hold my breath on that, so I decided to ask you about this in the meantime.

So, that is one issue, but the other issue is stated by Microsoft here:
https://support.microsoft.com/en-us/kb/2590447
the following:
"Exchange Online synchronizes connected accounts every hour. This means that messages from a connected account are downloaded to Outlook Web App every hour. Currently, there's no method to change the synchronization interval for connected accounts. "

If synchronization only happens once an hour, then what possible use is a 'connected account' then if you have to wait an hour for each reply to come in? I understand that Microsoft states you can log into outlook.live.com and it will sync sooner than that, but for Outlook 2016 users, this is not practical.

Ultimately, I want to use Outlook 2016 to handle all email, using the web interface only as needed for setting changes or whatever. But so far, I am only doing this configuration strictly through outlook.live.com, just to make sure it works on their side before I concern myself with getting Outlook 2016 configured.

This looks like a major fail to have a 'connected account' that only syncs once an hour, and doesn't allow you to send email though it. This can't be "by design' or whatever other euphemism they want to use to describe a feature that doesn't work as expected.

I've searched all over the web for info on this issue, and so far, all I've found is outdated MS articles with incorrect information, scores of threads repeating outdated/incorrect info, and an Answer tech that couldn't figure it out while connected remotely. I think if MS tier 2 support can't solve this, you are my last hope for answers.

Thank you, Diane, for any light you can shed on this dilemma.

PS. as a side note, I have a gmx.com account that aggregates emails from a totally separate/unrelated Comcast account, and it lets me send messages through it as if I am sending directly from Comcast webmail. No 1 hour delay in new emails being retrieved, and no problem sending Comcast email. I don't know why this is such a problem for Microsoft in this case.

PPS. I've referred to 'outlook.live.com' because I did not want to confuse the reader into thinking this is a problem with the desktop application, and because I can't keep up with all the name changes MS has thought up over the last few years. I do not own/operate a MS Exchange server, and nothing I've described here pertains to the desktop application, Outlook 2016. All I have is the $99/yr Office 365 Home subscription.

 

[Thomas Inman]

For anyone interested in a follow up to this issue, I exchanged emails with MS Answer-Techs about this, and found them to be unhelpful, wasting countless hours of my time by sending troubleshooting documents that did not pertain to the issue at hand.

Repeatedly explaining the issue to each new person that worked the trouble ticket was a fruitless effort. I don't know who those people are or what qualifies them to do tech support, but asking you endless questions about what platform you're on, what version of Office you have installed, check for viruses/malware, blah blah, I think, serves only to discourage users from actually asking for help when something isn't working correctly. (note: issue is/was not with their desktop software, it is entirely on the server side)

My "solution", if you can call it that, was to simply forget all about using the Connected Accounts function of Outlook.com to send/receive email through a non-MS account. Instead, I configured the user's Comcast account as IMAP, and created a new Outlook.com user account to be used only for syncing the user's Outlook 2016 calendar, contacts, and tasks. So, basically, you have two accounts configured in Outlook 2016 - the one you want to send/receive email with, and one that syncs across your various devices.

What I wanted to do was have his Comcast account set up as a Connected Account so he could send/receive emails through the Outlook.com interface, and have only one EAS account configured in Outlook 2016.

For the record, to this day, I still get occasional emails from MS Answer-Techs asking if the problem has been resolved yet. The issue is reproducible on any Windows computer, regardless of version or choice of browsers. Yet, they are asking ME if it has been resolved! WTF?

Sadly, I did not receive any responses to my original post in this forum either. Hopefully, sharing my experiences will help someone avoid going down the same rabbit hole.

 

[Diane Poremsky]

I had that problem when the connect account wasn't authenticated (I forget what the exact status was) - i removed the account and added it back and it finally worked... but in all honesty, your solution is the best solution. Connected accounts will occasionally stop connecting and need to be restarted, they only check mail hourly.

I configured the user's Comcast account as IMAP, and created a new Outlook.com user account to be used only for syncing the user's Outlook 2016 calendar, contacts, and tasks. So, basically, you have two accounts configured in Outlook 2016 - the one you want to send/receive email with, and one that syncs across your various devices.

 

[Thomas Inman]

I know you're right about synching once per hour or so. I read that in a MS doc somewhere, and Gmail does the same thing. Makes you wonder how on earth a connected account is usable for anything. Unreliable, at best. Yet, this is a feature they use to entice users to create a new Outlook.com account.

I also went through the process of authenticating my machine using their authentication application, and I thought that was what would ultimately make the connected account start working. It did not. I recreated the same scenario with totally different accounts on two new vanilla machines. No difference. The connected account still would not send email. Just sits in the Drafts folder with an error message as I mentioned in the original post. The point is, this issue can be reproduced regardless of which computer you're on, or which email account you use as a Connected Account.

As a side note: My observation of MS Answer-Techs in action is that as employees, they are held accountable to respond to trouble tickets, but are not held accountable to actually resolve an issue. I must have received half a dozen emails from them asking if the problem was resolved (resolved by whom exactly?), and I respond politely that it has not. You'd think they would reply with some kind of instruction/suggestion/hint to resolve the issue, but all of my replies went unanswered.

For anyone that trades the equity markets, I shorted Apple from ~$121 down to ~$90/share in order to recoup countless hours of labor I've put into solving ridiculous iCloud issues. That investment paid me back in 1 month. Maybe it's time I short Microsoft stock too.