I just spent an hour or two in a furious state trying to set up SMTP relay with a G Suite domain, and it was stupidly frustrating because there was one little component stopping everything. Oh the rage!
My intent was simple: SMTP relay using a domain account for authentication and TLS. Should be easy.
When you look at the the instructions for setting up SMTP relay, they do appear on the surface pretty straight-forward:
Go to G Suite > Apps > Gmail > Advanced Settings
Make sure you’re at the top level of the OU structure (you should be)
Add “SMTP relay service” (it gives you a few options, in my case I want to use an account to authenticate, see below)
Then you configure your SMTP relay settings on your application to point to smtp-relay.gmail.com on port 587, input your SMTP authentication and then all done, right?
WRONG! You’re going to get continual authentication errors (Google’s SMTP error code “535 5.7.8”) and Google’s SMTP service will tell you to pound sand and send you to unhelpful help articles about having bad credentials.
You have to perform one more step not mentioned in the Google documentation (here’s where I found this fix): enable “Less secure app access” in your Google service SMTP account settings. Easiest way to get to it is go to Gmail > click on the service account profile > click ‘Manage your Google Account’ (tangent: why is ‘your’ not capitalized?) > then just search on the top for ‘Less secure app access’ and toggle the button to on. It looks like this:
That’s it! After that, SMTP relay will start working correctly.
Maybe this will help prevent some Hulk transformations.
(Update 20191220.1238 – Reworked some parts because I was in a rush last night).
A few weeks ago I had the pleasure of attending Microsoft Ignite 2017 in Orlando, Florida, one of the best and well-organized conferences I have ever attended. There were a ton of sessions to attend for people of all backgrounds in IT, so I couldn’t hit them all (thankfully they’re posting the sessions on YouTube).
It’s a juggling act at events like this to strike the balance between personal interest and getting information/training to add value to the organization that sends you, so I focused on Windows 10 Deployment, Azure IaaS, and whatever Powershell nuggets I could find. All three topics are too much for one post alone, so I wanted to dump some thoughts on one that stuck out the most: Windows 10 Deployment.
Creeping from the Old to the New: Windows 10 Deployment
Device deployment in the Microsoft world has been dominated by what they call “traditional IT”, which we in the SCCM/MDT world would just call imaging. The “traditional” method of deploying devices often involved a lot of preconfiguration before the device actually reached the end-users, often with BIOS updates/configs and the tried and true method of wipe and load.
Of course, at Microsoft Ignite, you’re going to get proselytized about the company’s newest technology, and the direction Microsoft is transitioning to is something they call “modern IT”. It’s best summarized in this slide from Michael Niehaus’session on deploying Windows 10:
In practice, what this actually looks like is a bit of gradient between on-premise and cloud-based services, but the direction Microsoft is taking is to move identity services to Azure Active Directory, device management to InTune, applications are deployed from the Windows Store, and updates are managed via Windows Updates for Business. The entire process initiated on end-devices after a user logs into a device with their email and password with an Internet connection, removing the need for special provisioning. The entire process is summarized into what Microsoft calls “Windows AutoPilot“.
However, what I took from AutoPilot and all the deployment sessions was that while Microsoft would love for organizations to move their deployments online and sign-up for that recurring revenue, they know this is still a little ways off and doesn’t offer the feature parity of AD/SCCM. So instead, they’ve designed InTune and SCCM to really work in what they call “co-existence”, which comes from using the old and new methods together as a form of transition (to varying degrees): InTune-SCCM-AAD, or InTune-SCCM-AD, or (insert combo). The idea here is to not go full cloud, but transition to it to some degree.
One of the deployment MVPs who represented Microsoft explained it to me like this. Microsoft’s story about centralized Windows management has been largely one-sided for over 20 years: SCCM or nothing. There was no middle-ground between nothing and SCCM (although you could cobble-up some combination of AD, MDT, and scripts). InTune, AutoPilot, Windows Store — the combination of it all presents a middle-ground, a sort of gradient to centralized management. If you want a lot of control over your devices, continue using SCCM; if you want something simple, you have InTune now.
I think what Microsoft has done is make an interesting case for “modern” deployment, but until their on-premise AD component is deployed and fully-tested, I just don’t see a compelling case to even try InTune yet. The current deployment process, while not perfect, works pretty well, so this would have to be hardware that is proven to work well. Past experience makes me skeptical that hardware will work as well and consistently as SCCM OSD does (then again, I’m not working with users across the globe, so maybe there’s a better case to be made in that scenario).
Modern Windows 10 Deployment and Education
Bringing this closer to the industry I currently work in, Microsoft’s case for Windows 10 deployment and management for education is strong and better than ever before. Windows AutoPilot is indeed a great way to deploy devices (no matter which way you approach it), Azure AD and Office 365 are stellar products, OneNote is awesome (best education tool I’ve seen), Microsoft Teams looks amazing (especially with its takeover of Skype for Business and integration with Microsoft Classroom), and Microsoft’s licensing is making a big change. The classroom tools are indeed there, and management is as easy as G Suite (IMO).
However, I can’t help but ask: has the ship already sailed for a lot of K-12 organizations? I mean, Microsoft certainly has this great product for K-12, but a lot of organizations have already made massive investments in their device purchases, the technology choices they’re using in the classroom, and the email/cloud platform that they’re running applications with. These organizations already have inertia in the direction of these choices, so does Microsoft have enough to unbalance this forward motion?
I personally don’t think so, at least for the G Suite organizations. These organizations chose G Suite (or Google Apps at the time) largely because they could purchase educational devices for cheap, thereby getting more devices into student’s hands, and Google’s services (which users organically learned to use over the years) was free. Around the same time, Office 365 licensing was confusing, and while there were some free options, the service parity for device management just wasn’t there compared to G Suite.
Maybe it’s the Microsoft Ignite kool-aid in my system, but Microsoft has a better case for it’s products than Google with it’s licensing combos, or maybe Microsoft is just better at marketing and promoting it’s platform than Google. In the education world, I hardly ever hear from Google themselves promoting their products, it’s always someone doing something randomly. Microsoft constantly makes contact with my org, but Google — not a peep.
(I’ve decided to change things up a little bit and add some tech opinions every now and then, especially since I’ve changed jobs and I am now working for a medium-large school district. I’m titling these, “Quick Thoughts” that I’m going to write during my lunch breaks. Perhaps first of many…)
As a systems engineer for a school district, one of the tasks I have is to assist in the configuration and maintenance of our end-users working with whatever tools are offered by and Microsoft and Google. At our school district, we are primarily a G Suite shop, with students and staff working within the G Suite apps, but what about the tools that Microsoft offers with Office 365 such as OneNote, Microsoft Classroom, and others? How do we, as the administrators of such tools, give these users the ability to work with whatever tools they want?
It seems a bit difficult at times because each platform, G Suite and Office 365, appear to really rely on their email services to leverage alerts and messaging, so if you miss a conversation in Skype for Business, you’ll only receive the email within your Exchange email, but you won’t receive it on the Gmail side. I’m not entirely sure this is a two-way street on the Google side, as I’ve seem to have no problems logging into services like Meetup.com with my G Suite account, but receive my emails from the account on my Office 365 account.
It seems like Google is playing fair with their services, but Microsoft certainly doesn’t seem that way. So do we move email services to Office 365, and will this provide our users a better experience?
I’m not sure, and of course I don’t make those decisions, but I do think about it.
Maybe the more accurate question is “How cleanly can users operate in both worlds?” Sadly, while Google appears to behave better than Microsoft, this behavior actually hurts them a little bit for organizations like ours that want to use both services, as it forces us to consider using Exchange services for email to make the overall user experience better.
Microsoft seems to be the bad actor in this situation because they’re services don’t behave well with email systems other than Exchange. Even on-premise Exchange takes a bit of work to get working with Office 365 services.
Microsoft really wants all the business and tries to push organizations that way, but Google plays better with others, and Google’s platform seems to be more easily adopted by teachers than Microsoft’s (especially evident by how much marketing Microsoft has to do for education).
Of course, I’m assuming Google does play nice, but I haven’t tested every Google product, but Google has shown signs of not playing nice too, like dropping XMPP support for Hangouts, but that’s another conversation, and I’ve got to head back to work.