Can't send email in outlook.com

Outlook version
Outlook on the web
Email Account
Outlook.com (as MS Exchange)
#1
Hi,
I am unable to send messages in outlook.com. Instead they got to "draft" folder. I get this error message:

This message can't be sent right now. Please try again later. An internal server error occurred. The operation failed., Sending email is temporarily unavailable for this acccount. Details: ConnectedAccount:Address:mescovitz@gmail.com, Guid:9e15dc0d-c6ad-473c-a8c4-5efa2cab27a5, Status:Failed, Flags:RemoteSendEnabled, SendEnabled, MoveSentMessagesToSentItemsFolder.

Thank you!
Myron
 
Outlook version
Outlook on the web
Email Account
Outlook.com (as MS Exchange)
#3
How long since you were last able to send messages from the connected account? Is it working today? There are sometimes transient errors that delay the send for a few minutes.
How long since you were last able to send messages from the connected account? Is it working today? There are sometimes transient errors that delay the send for a few minutes.
It's not consistent. Sometimes it sends and sometimes it doesn't. It's
been so frustrating, I've considered switching to another email service. Would it help if I said that when it happens, and I'm checking the settings, I go to "connected accounts" and I notice that the latest attempt to sync with gmail, it says it failed.
 
Outlook version
Outlook on the web
Email Account
Outlook.com (as MS Exchange)
#4
Also, I forgot to mention, the app on my phone sends messages just fine. It's only on a computer, any computer.
 
Outlook version
Outlook 2016 32 bit
Email Account
Office 365 Exchange
#5
I go to "connected accounts" and I notice that the latest attempt to sync with gmail, it says it failed.
I'm not sure it helps... but it explains why the message didn't send. Best guess is gmail limits the number of connection microsoft can make to their accounts at one time.
 
Outlook version
Outlook on the web
Email Account
Outlook.com (as MS Exchange)
#7
I'm not sure. I only need my outlook account to show my gmail emails. I don't need to send through gmail. Is that what I'm doing? If that's the case, how can I change the settings to send from outlook.
 
Outlook version
Outlook 2016 32 bit
Email Account
Office 365 Exchange
#8
it looks like you need to remove the account and reconnect it in outlook.com - i diont see a way to change the settings once its added to outlook.com. (This account is using the new outlook.com interface, the dialog should be similar in the old interface).

2018-06-11_11-54-29.png
 
Outlook version
Outlook 2016 32 bit
Email Account
Office 365 Exchange
#9
Actually, scratch that - it will send from gmail by default. :( (if i could read dialogs, i'd be dangerous :))

it doesn't look like you can change it in outlook.com - but if you forward from gmail ot outlook.com, replies will be from outlook.com. It's not a good experience though, IMHO and outlook.com tends to bounce the forwards as spam (for bulk mail and actual spam).
 
Outlook version
Outlook on the web
Email Account
Outlook.com (as MS Exchange)
#10
Actually, scratch that - it will send from gmail by default. :( (if i could read dialogs, i'd be dangerous :))

it doesn't look like you can change it in outlook.com - but if you forward from gmail ot outlook.com, replies will be from outlook.com. It's not a good experience though, IMHO and outlook.com tends to bounce the forwards as spam (for bulk mail and actual spam).
So you're saying there is not much I can do about it?
 

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