My Gmail to Outlook migration ends in failure

My current theory with apps and services is that Microsoft is shaping up into an appealing neutral zone between Apple’s walled garden of deteriorating software quality, and Google’s endless data slurping.

I’ve been a Gmail customer for something close to 20 years. It was groundbreaking at launch thanks to the unique proposition of almost-limitless storage, back when others were offering miserly amounts like 5Mb. But we all know that Google is data-mining our mailboxes to fuel their advertising system, and I don’t like that in a personal messaging system like email.

What finally persuaded me to try a move to is the premium experience that comes with my Office 365 subscription. Not only does this provide a terabyte of mail storage, but the web interface is completely ad-free. The web interface is also superb – it’s beautifully designed and blazing fast.

Taking the plunge

So, two days ago, I exported my data and switched over. The basic process was to link Gmail in Outlook and let it copy my messages across. It did this amazingly quickly, but the reason why is that it doesn’t copy the All Mail folder, which in my case contained nearly 5,000 messages. To fix this, I used Google Takeout to export the folder. Getting this data dump into Outlook took a bit of trickery – Outlook speaks .pst files and Google Takeout spits out .mbox files. Luckily, macOS Mail supports importing .mbox files so I imported it to a local mailbox and then copied all those messages to the archive folder of Outlook. This took a while, but completed successfully.

The final part was some configuration to make the move final. Changing my Windows, iOS and Mac mail clients over, then setting Gmail to forward messages to Outlook and then delete them. Then the fun part – deleting all my messages from Gmail ?

Outlook is great for email…

At first, it all looked great. I prefer the folder-based Outlook approach to email management, rather than Gmail’s slightly-odd systems of labels and the “All Mail” folder. All my mail clients seemed very happy too, not having to deal with some of the IMAP wierdness you get with Gmail. Even better, using the excellent Outlook client on my phone means that for the first time in years, I get email notifications again. You may remember that this is something that Google and Apple managed to break between them a few years ago when Google stopped supporting an old protocol that Apple Mail was using.

Email needs contacts

Soon though, there was a problem. As well as messages, I’d also exported my contacts from Gmail to Outlook. The import had worked fine, but the next day I noticed that none of my contacts had photos. That makes sense because the export file was a CSV. So I tried another approach of exporting and re-importing them using the Mac Contacts app. This export file definitely includes images – I can see them base64 encoded in the export file – but Contacts can’t save them to Outlook. It was time to switch to manual mode. The Google Takeout archive had thoughtfully provided a folder of .jpg files, so it would be easy enough to edit each contact and add the image back in.

Firstly, I tried editing via the macOS Contacts app, but it still doesn’t work. It lets me select an image and save it, but when the list is refreshed the image isn’t there. Disappointing but it could quite easily be a bug with the Outlook interface of Contacts, rather than an actual Outlook problem. Using the Outlook web client would surely do the job wouldn’t it?

Actually, it doesn’t. Add a photo to a contact and a nice popup appears, letting you select a photo, then move and resize it. Then a “Done” button appears with a green tick. Perfect, except it also doesn’t save.

My last chance was to boot up my Windows 10 machine and try to use the People app. That was a complete non-starter because it only lets me select a photo from my Windows Photo library, and I’ve got a feeling it wouldn’t push the image up to Outlook.

Having photos on contacts might seem like a small feature, but I think it’s important. Look at messaging apps – they all have contact images against conversations now, and seeing a column of circles with initials in them doesn’t look great.

So there we go – an excellent email system crippled by broken contacts management. Now to figure out how to get all this stuff back into Gmail.

Dig those initial-filled roundels

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