Unable to get emails working in Helpdesk Server VM

spiceuser-gfyul · 2021-06-16T08:56:51.000Z

I have read multiple posts and spent a fair amount of time trying to resolve this but I am struggling to know what to try next.

We are in the process of moving from Spiceworks Desktop to the appliance help desk server and I cannot get emails working through Office 365.

I have tried the same settings used by the desktop and they don’t work for either incoming or outgoing and have tried many different things based on reading the community and help guides.

My current setup:

VHD running in Hyper-V

IMAP enabled on Office 365 account

For incoming I have tried https://outlook.office365.com and outlook.office365.com

Password verified in OWA

Port 993 for incoming and 587 for smtp

SSL and STARTLS enabled

Any pointers on what to try next?

Suzanne-Spiceworks · 2021-06-16T09:56:44.000Z

Tagging support for you.

@spiceworks-support-team

timgirvin · 2021-06-16T11:55:39.000Z

wolvesphil:

I have read multiple posts and spent a fair amount of time trying to resolve this but I am struggling to know what to try next.

We are in the process of moving from Spiceworks Desktop to the appliance help desk server and I cannot get emails working through Office 365.

I have tried the same settings used by the desktop and they don’t work for either incoming or outgoing and have tried many different things based on reading the community and help guides.

My current setup:

VHD running in Hyper-V

IMAP enabled on Office 365 account

For incoming I have tried https://outlook.office365.com and outlook.office365.com

Password verified in OWA

Port 993 for incoming and 587 for smtp

SSL and STARTLS enabled

Any pointers on what to try next?

Thanks Suzanne for forwarding to support - We all seem to be missing a key ingredient/s to the secret sauce for it to work the first, second, third, time… Sounds like the install guide needs to be revised to answer the numerous questions about email setup options and requirements. Especially when email provider requires modern authentication like M365.

Brendan-Spiceworks · 2021-06-16T13:48:04.000Z

The documentation here is still accurate, to my knowledge. Pay close attention to the SSL and StartTLS settings.

https://community.spiceworks.com/support/help-desk-server/docs/email

The modern authentication bit may not be resolved soon:

What’s going on with Spiceworks Tools & Apps in 2021? Spiceworks Support

Hi SpiceHeads, While we’ve been posting various updates as of late, we know many of you are curious about the direction of the Spiceworks Tools & Apps. We want to make sure you’re not just aware of our plans but are also a part of the conversation. The road behind us Our primary focus this year is on helping our members migrate off of the legacy Desktop application. Back in 2018, we announced that we were no longer going to be improving Spiceworks Desktop after version 7.5 and that version 8.0…

timgirvin · 2021-06-16T14:29:20.000Z

Brendan - The email setup info has definitely been update since my last look(pre-COVID). Thanks

We ended up adding and internal SMTP gateway for outbound email and an internal IMAP server for inbound email. Both are connected to M365 via transport rules to manage to mail flow. A more complex setup but works for Spiceworks or other internal systems that can’t authenticate using newer protocols(like MFPs).

Brendan-Spiceworks · 2021-06-16T14:41:24.000Z

Thanks for the update - I’m glad you were able to sort it out!

spiceuser-gfyul · 2021-06-17T06:43:10.000Z

I have managed to get incoming mail working, however the mail remains in the inbox as read rather than deleted as it did on spiceworks desktop - is this correct?

I am still struggling with smtp through 365

Brendan-Spiceworks · 2021-06-17T12:54:25.000Z

Mail remaining in the inbox is likely an IMAP setting - you can typically set the behavior you want.