Shift to MS365 for four nonprofit PCs

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Microsoft in its benevolence (via TechSoup) has gifted my small non-profit the (software) keys to the castle. I am the default [volunteer] sysadmin/bottle-washer and capable of following a technological path to its bitter end, BUT am a social worker by day.

We have 4 PCs and I had hoped that a switch to MS365 might get closer to a “set-it and forget-it” scenario.  We do NOTHING sophisticated technologically and while I do have specific problems to solve, this question is more general…

What is the best path to smooth functioning PCs without dedicated box-by-box management?

I can remotely log into each PC, and do so [as often as possible but not often enough] to apply updates, verify backups are taking place, and to my immediate concern, manage Office app versions/functionality.

MS has provided me access to an astonishing new world of capabilities, and I’ve explored/poked/prodded and fiddled to my hearts content.  However, I continue to wrestle with such basic issues as “now that I’ve updated the Admin assistant’s machine/account to 365, is the local copy of Outlook updated?”

Truth be known, my IMMEDIATE concern is email deliverability and a secretary whose email (hosted on a shared-IP server with InMotion Hosting) can’t be reliably delivered to the board chair who uses a yahoo account. I’m on the cusp of pointing DNS MX records to the Exchange Online mail server but – though I *believe* I’ve thought through the consequences of doing so – I don’t have the experience to make that shift without great trepidation.

Back to the bigger picture – how can I move toward a system of lower-management computing for a small non-profit?  I have SO MANY technological options available, but lack the experience to know which avenues to pursue.  I’m a volunteer, so highly affordable, but… you get it by now.

Thanks for your thoughts!

Dean

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So where is your email hosted now? Do you already have a domain name?

Susan Bradley Patch Lady/Prudent patcher

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Hello Susan

Yes we have a custom domain and the mail server is hosted at InMotion Hosting. The email server is on a shared IP, which I know makes us vulnerable to the behavior of other clients using that IP.

Here’s a snippet from one recent response back from a receiving server (my emphasis):

Reporting-MTA: dns; se4-iad1.servconfig.com
Action: delayed
Final-Recipient: rfc822;xxxxxx@rocketmail.com
Status: 4.0.0
Remote-MTA: dns; mta6.am0.yahoodns.net
Diagnostic-Code: smtp; 421 4.7.0 [TSS04] Messages from 199.250.217.13 temporarily deferred due to unexpected volume or user complaints – 4.16.55.1; see https://postmaster.yahooinc.<wbr />com/error-codes

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You’re going to have to edit your mx, cname and some txt records at Inmotion with the info supplied by MS. Importing your current emails is another whole process. MS should have documentation to help you along but if you aren’t familiar with it, it might be a good idea to get someone experienced and pay them to do it for you.

Never Say Never

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Thank you cyberSAR –

I have successfully edited DNS records in the past, that part of the change seems rather straightforward. Bigger picture, can we expect the shift to MS serving will fix our deliverability problem?

I’ve tried to wrangle .pst files in the past… now THAT is something I might want to hire done!

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I would think the ms servers will be better for delivery. They do sometimes bounce, but usually rectified much faster. All of the clients we moved to MS used IMAP so the import was a bit more involved. I would just advise that you grab a full backup at inmotion before you start. Not sure, but I think they are cpanel so the backup is very easy.

Make sure you have all users’ passwords too as it makes things easier going forward. Of course, you could change them then notify them of the change. Good luck!

Never Say Never

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deanm

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Thank you cyberSAR, that is relevant experience.  Anyone else able to confirm? This thread has veered completely into the email deliverability topic… will a move to Microsoft email hosting fix our deliverability issues? How about for newsletters sent to <100 recipients?

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Not sure on newsletters with less than 100 recipients. We run a separate server and dedicated newsletter software for our clients’ newsletters as we don’t want their primary emails being impacted, although some of their billing software does send well over 500 emails 1st and 15th of the month but we haven’t had any issues. We tweak it to send on a delayed schedule though.

If you are sending to multiple recipients as copy or BCC many servers balk at that. Also, we find MUCH better delivery and fewer issues after setting up DMARC for the domain (subdomain) sending the newsletters.

HTH

Never Say Never

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GREAT info. It hadn’t occurred to me to create a subdomain to “protect” the primary domain. Still resolving to the same IP address as the primary server I assume?

Also, you hit the nail on the head with the BCC sending scheme.  That is how we send presently. Does the newsletter software break each recipient out into their own “direct” email?  Care to share what software you use?

We’ve considered using Constant Contact or MailChimp, et. al.  (and with our nonprofit status might get those services “donated”). Simplicity is king here – our part-time secretary needs to operate the system and while she IS competent, there is little sense asking her to learn anything complex.

Thanks for your help!

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I should have been a bit more clear on the newsletter domain. We either use a separate domain of the client or a subdomain of a generic domain we own personalized for the client. Example yourdomain.ourmaillistdomain.com I prefer that as it’s easier for me to manage 🙂 They are on a different server and ip. On getting an occasional report of spam I deal with it immediately and have not had any delivery issues while some clients have 20,000 and more subscribers and send multiple newsletters per week.

I have used Dada Mail for many years and tweaked it quite a bit. Some clients create their newsletter in Dada, some use a web editor and send the webpage they created and some send a feed from their wordpress site. Has worked very well for us.
https://dadamailproject.com/

Never Say Never

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Does the newsletter software break each recipient out into their own “direct” email?

Sorry, didn’t address this as I’m cooking some liver and grits and got sidetracked  🙂 Yes, it does. Also the software has an html WYSIWYG editor or two built in. Very easy to use for non-techies

Never Say Never

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