Office365 WHD keeps disconnecting from SMTP

dcachia

Hi all

We are trying to use SMTP via Office365 for our Web Helpdesk.

SMTP Server - outlook.office365.com - 587 SSL

Simple Authentication - Simple

SMTP Username - The Email Address

Password - *****

Friendly name - The Email Address

Web Help Desk Email Address - The Email Address

Accepted Domains: empty

incoming mail account - The Email Address

It authenticates (green light)

Then a few minutes later I will come back and it will be red.

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dcachia

12.6 - Build #12.6.0.738

justin.gray

Under Setup > Options > Email Optiions, at the top what do you have for 'Connection Timeout'? You can try increasing this value to see if that resolves the issue.

dcachia

Could you suggest a timeout time? It was 30 seconds.

Dave Cachia, M.Sc

Senior Systems Consultant, Information Technology

Cell. 905.244.9634

Office. 905.576.8711 ext.2913

dcachia@lakeridgehealth.on.ca

Excellence – every moment, every day.

www.lakeridgehealth.on.ca

image001.png

dcachia

Still appears to be an issue after changing timeout period to 360.

9/24/18

12:49 pm

Couldn't connect to host, port: outlook.office365.com, 587; timeout -1

Excellence – every moment, every day.

www.lakeridgehealth.on.ca

image001.png

volodymyr.prystaiko

Yo can untick checkbox "SSL" it will connect via STARTTLS.

dcachia

Office365 Support says it is an issue with TLS1.2 - does anything need to be on the WHD side to enable TLS1.2?

volodymyr.prystaiko

It should work from scratch. WHD 12.6.0 support TLS1.2.

dcachia

Well.. it keeps disconnecting. I am able to SMTP authenticate just fine from my PC.

WHD keeps dropping its connection to the SMTP service.

dcachia

Encountered error while attempting to send email: com.sun.mail.smtp.SMTPSendFailedException: 530 5.7.57 SMTP; Client was not authenticated to send anonymous mail during MAIL FROM [YTOPR0101CA0011.CANPRD01.PROD.OUTLOOK.COM]

Encountered error while attempting to create transport for sending email: com.macsdesign.whd.util.EmailMessageController$CouldNotCreateTransportException: Could not create transport for E-Mail messages: Connection refused: connect

volodymyr.prystaiko

Did you configure Email sending. In Setup->E-mails->Outgong Mail Accounts

dcachia

Yes.. of course.

Dave Cachia, M.Sc

Senior Systems Consultant, Information Technology

T. 905.576.8711 ext.2913

C. 905.244.9634

dcachia@lakeridgehealth.on.ca

jimmy.kargoll

Try IMAP as a Test or set O365 Exchange port to 25 instead of 587

IMAP O365.JPG

dcachia

Tried it. Still an issue.

gfsutherland

Port 25 should work.

Anonymous authentication?

Also verify accepted domains.

dcachia

I don't think Office365 is going to relay your mail if you're not authenticated.

All domains should be accepted, we receive tickets via an auto-ticket generator (email)

zbelhat

dcachia Check if the account gets locked - I have seen with Exchange 2010 so it might be also happening on Office365

dcachia

Account is not blocked.

fluffy_midnight

Hi dcachia,

I believe this is the exact same issue that came up when 12.5 came out, the issue is related to the connection timeout that occurs when the Office 365 relay switches from one host to another.

Here's a thread that david@unipresssoftware.com raised, and continued to discuss between the community and directly with SolarWinds until it got fixed soon after in 12.5.1: Office 365

-Midnight

dcachia

I checked it out - looks like it was an issue with intermittent incoming messages - not outgoing. Issue is only with outgoing mail here.

Dave Cachia, M.Sc

Senior Systems Consultant, Information Technology

T. 905.576.8711 ext.2913

C. 905.244.9634

dcachia@lakeridgehealth.on.ca

fruiz

I am having the same issue. We manually switch between port 587 SSL to 587 no SSL, when that doesn't work we switch between port 25 SSL and port 25 no SSL. This it is an extremely annoying problem and I have sat on the phone for hours with customer support for multiple days and no resolution, the engineers claim it is an Exchange issue and I need to contact my administrator ....-__-

garymccune

This exact problem is an ongoing issue for us as well, over the last 2 years.
However, our norm is working and drops are intermittent.

Outgoing emails are fine, suddenly connection stops working. This is unpredictable and I've seen it 4 times in one day and not at all for a month. It's happened about 4 times this week though, which is why I'm here.
WORKAROUND: In Outbound mail settings, we can uncheck the checkbox for SSL. Then, approximately 3-5 minutes later, we recheck SSL and it connects again. If we do it earlier it just keeps failing. We can keep trying until it works but typically 3-5 minutes seems it will resolve the connection again.

It's not the account: Account never is locked, can establish connect to the account from other avenues.
Restarting the WHD or even the Server does not solve it.

Here's the same issue from 2017- no resolution:
O365 & dropping email connections in WHD

https://thwack.solarwinds.com/message/380078#38007

Seeing same commentary here as the old 2017 forum post:
That this issue was solved in an updated version of WHD which is not correct. We are currently on version 12.6.0.738 and the issue is alive and well.

That 2017 forum post references an even older call-out to the issue at
https://support.solarwinds.com/Success_Center/Web_Help_Desk_(WHD)/Intermittent_connection_to_the_Incoming_Mail_account_using_Office_365?CMPSource=THW&CMP=REFDOM
but that post has been removed.

I'm pondering making another ticket about this, for 2019. Neither this Sep 2018 one nor the older 2017 is marked as resolved, just forgotten.
If anyone has ever fixed this issue please post what you've done!!