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Moving to WordPress.com and Office 365

How we moved from a dedicated server to letting WordPress.com handle it all for us.

PigPog was hosted on a dedicated server, hosted by AIT, running the open source WordPress.org. Sam and I both had email forwarded by AIT to our iCloud accounts.

Now, the site is hosted on WordPress.com, and our email is handled by Microsoft Office 365.

If you’re just here for the photos, there’s no reason you should care about any of this (except the photos should actually work now), but I figured I’d write a bit about the experience, in case it’s useful for anyone considering similar things.

The Problem(s)

Cost

A dedicated web server is expensive. AIT was a choice we made over twenty years ago, before there were many hosting companies in the UK, and there were limited options. Given that, it’s worked out ok. They’ve remained one of the cheapest for what they provide, and the support was generally pretty good. Usually quick and efficient, and always seemed more human than I’d expect from a big hosting company. But for a personal blog, it was a bit much.

At one point, PigPog had advertising and affiliate links, and actually brought in a bit of money, but it doesn’t any more. At the time of writing, its entire income is $1 a month from Patreon. Thank you, Rosi!

Photos Not Appearing

I love the new WordPress block editor, and the beautiful layouts it makes so easy to do. And I love doing big posts with lots of photos. But they just didn’t work.

Photos would take many refreshes of the page to start appearing, and a few days later, they’d vanish again. No idea what the problem was. Troubleshooting was difficult with so many variables. There’s the hosting, WordPress itself, the Jetpack plugin, Jetpack’s CDN that resizes and serves the photos, the lazy loading feature, and Cloudflare.

My best guess was that AIT were blocking one of the servers Jetpack used to fetch the images, but they said not. Maybe our server just didn’t respond quickly enough to some of the requests, and Jetpack gave up easily. No idea.

But for a site that’s all about showing off photos, it was, perhaps, less than ideal.

eMail was Unreliable and From The Wrong Place

It wasn’t a really big deal to us, but the forwarding setup meant we didn’t seem to get email from some places. Only one or two, but enough to notice. And our emails came from our iCloud addresses, not pigpog.com. Not ideal, but also not a big problem for us.

Complexity and Updates

WordPress updates were our own problem to do. It’s pretty easy, but if something went wrong at any point, it would be my problem to solve. It’s the sort of thing I used to do for fun, but now I really just want it to be easy.

Things I Considered

Hosting

I did, of course, consider just sticking to what we already had, and try to sort out the image problems, and living with the cost. I’m lazy with that sort of thing, so it was very tempting.

Since I’ve listened to a few podcasts, and watched a few videos on YouTube, I considered SquareSpace. It looks pretty good. But it didn’t look like it offered anything I wanted that WordPress didn’t offer, and I already knew and used WordPress.

The option I ended up with was sticking with WordPress, which I love, but moving to a WordPress installation hosted by WordPress.com. There really shouldn’t be anyone better placed to run WordPress. Because it’s just a copy of WordPress you have access too, there’s nothing much to fiddle with, and everything it runs on is going to be what they consider the best possible version. No more worrying about PHP or MySQL being a bit too old to work as well as it should.

I spent quite a while setting the site up, and playing with themes. I tried creating posts and deleting them again many times, to find the best ways to do it.

I was in the situation of not really having found a theme I really liked, but there were ones that were good enough to do the job. But then one day, the new Twenty Twenty theme appeared, and it’s really nice. At the time of writing, at least, that’s what you’re looking at.

eMail

It we were using a different host, we’d have to do email at least slightly differently. But not much. We had email pointing to the AIT server, with it set to forward everything to our iCloud accounts.

We moved the domain to 123-Reg first, though, and they also have email forwarding, so we could just keep doing that. The simplest way of doing WordPress.com hosting is to point everything to their nameservers, though, which would prevent that from working. But they also do email forwarding, so it still didn’t have to change much.

But since we’d had some problems with emails not arriving, and didn’t really like them coming from our iCloud addresses instead of our ‘real’ addresses @pigpog.com, it was worth looking at options.

Making a decision took a bit more doing than I’d expected. I knew Office 365 and Google Suite were two options, but Office 365 wasn’t cheap, and surprisingly to me, Google Suite wasn’t any cheaper. We only really wanted mail, with decent sized mailboxes. Working well as an IMAP server was fine, as long as we weren’t limited to web-based only. And we both mostly use iOS and iPadOS now, so no real need for desktop apps.

I thought there would be cheaper options. And, to be fair, there were, but none of them seemed to quite do what we wanted, or were a bit limited in size if you kept to the low-cost versions.

So my aversion to giving money to Google held out, and Microsoft won. There’s a ‘business’ account for Office 365 that doesn’t include any desktop apps, and it’s a lot cheaper than the ‘full’ version, so we went for that. It would be nice to have the full version of Outlook on the Mac, but only occasionally, and to be honest, the full version of Outlook is awful. It just sometimes does stuff that’s harder with the iOS/iPadOS version.

The only time so far I’ve missed the full desktop version was when I’d imported all the mail, and wanted to move an archive of many years worth of mail from one folder to another. Didn’t seem to be at all feasible on the iPad, and was a bit painfully manual on the web-based version of Outlook. I’ve done similar things at work with full Outlook for Windows, though, and it’s pretty tough going there too.

Outlook is quite good on the iPhone, and pretty nice on the iPad.

The ‘home’ version of Office 365 is quite a bit cheaper, but you can’t add a domain to it, so we’d be back to forwarding and our email coming from much worse-looking addresses than our iCloud ones.

The accounts also come with 1Tb of storage each, and while the OneDrive app doesn’t seem very usable so far, it should be possible to use that as storage from our Synology NAS, so it won’t be wasted. And I’ve got emails ok from places where they used to fall into a bit bucket somewhere never to be seen.

iCloud email can be set to forward automatically, so I don’t miss any mail that goes to there – just set the forwarding through iCloud.com.

Making the Change

This was where things got quite long-winded, so I’ll keep the description short. I thought at first I’d just export the site from WordPress and import it to the new host. But the exports I created wouldn’t import. I could probably have broken it into chunks, but I started thinking about the years of mess I’d be bringing in, and decided on a fresh start. Build every post fresh on the new site, copying just the content I actually wanted to bring over. It would take a lot of time, but there were thousands of posts that just weren’t relevant to anything any more, and I felt pretty good about just losing the lot.

So that’s what I did. Created a new site, and started creating posts. It gave me a good chance to think about what’s important, and to review how I actually create posts, and I took the time to build the systems and workflows behind the scenes to do these things better and faster. I’ll probably write more about this stuff later, but the shoots are all in a database now, so I can track all the information about where, when, with who, and how, ready to write up a post.

I still love WordPress, and in fact, love it all the more now it’s actually working well. I can do every part of the process using my iPad, so I don’t need to use a laptop at all any more. I can work pretty much anywhere.

I wouldn’t go so far as to say I love Outlook on the iPad, but it’s quite good. Apple Mail can connect to Exchange quite nicely, too, so I’d always have that option if I wanted to, but Outlook is good enough, and keeps getting better.

It’s worth mentioning too how easy the combination of Office 365 and WordPress is to set up. When adding a domain, Microsoft gives you a code to add as a text record to the domain. WordPress gives you a box to paste that into. Once you’ve done that and returned to Microsoft, they recognise that you’re using WordPress nameservers for the domain, and lets you grant Microsoft permission to make the changes needed to the domain automatically. A few seconds later, it’s all done.

Overall, it feels like we now have everything based on the best available answers for now, instead of the results of the best we could find 20 years ago. It’s nice.

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