I’ve used Hotmail from the late 90s. All my friends and family use Gmail and I feel like a dinosaur with clunky old Hotmail. Apart from looking like I’ve finally entered the 21st century, what are the benefits of switching from Hotmail to Gmail? And, given everyone I’ve ever known has my Hotmail address, and I have so many old emails in my Hotmail inbox, how on earth could I switch? T

I was one of Gmail’s first public users in 2004 and spent a decade recommending Hotmail users to switch. I almost switched back in 2013, but both services have changed a lot since then. I now think you should have both services, with one acting as a backup, though you could also back up to Yahoo.

Ideally, you should use your own domain name for your main address. Unfortunately, neither Hotmail nor Gmail provides that feature free, though to some extent you can fake it with an alias. See below ….

Hotmail and Outlook.com

Today, I can at least guarantee that you are not using Hotmail. Microsoft closed that service years ago, and all Hotmail users are using its current service at Outlook.com. Technically, Outlook.com is newer than Gmail, though both services are updated all too frequently.

You are, of course, still using a Hotmail address. However, if you switched to using a new Outlook.com address, you would still be using exactly the same email service. In fact, the simplest way to remove the Hotmail “stigma” would be to add an Outlook.com address and use both from the same mailbox.

To do this, log into Hotmail and then paste https://account.live.com/AddAssocId into the address bar. (You can get to it via the full Settings page, Email, Sync email etc but it’s complicated.) Create an alias in the form myname@outlook.com, and set this as your primary email address.

You can now use the same inbox to send emails from both your old Hotmail and your new Outlook.com addresses, and switch between them.

If you email everyone from your Outlook.com address, most people will start using it eventually. However, anything sent to your Hotmail address will still arrive in the same inbox, so it doesn’t really matter. Microsoft has supported Hotmail addresses since it bought the service in 1997, and I don’t expect it will ever stop supporting them.

Note that you can also add aliases for any of your old email addresses. This might be handy if you have one you rarely use. Set it to forward all incoming emails to your Hotmail/Outlook.com inbox and reply from there.

Gmail v Hotmail

In the beginning, Gmail had several significant advantages over Hotmail. The main one was that it offered 500 times as much storage: 1GB! Gmail also had much better search and spam blocking, and it worked like an app rather than an HTML web page. (HoTMaiL got its name from HTML.) This made Gmail faster and more responsive.

Many iterations later, the two services are much closer. I like the fact that you can set up Outlook.com to work much like Outlook, the email program from Microsoft Office. Outlook.com still has folders instead of Gmail’s labels. Outlook.com even has the edge in offering more storage. Both services now provide 15GB. However, Outlook.com’s email storage is in addition to the free 5GB you get with OneDrive, whereas Gmail shares its 15GB with Google Drive.

At the moment, I prefer Gmail. It’s still faster; its search and spam-blocking still work better. Most importantly, Gmail still paginates emails, which means I can easily skip from the second page of search results to p500 (emails 24,951-25,000). This is useful when you have 250,000 or more emails in your inbox. You’ll never scroll back to 2004.

Switching to Gmail

If you want to switch from Hotmail to Gmail, or vice versa, then you have to open a new account. The hardest part is finding a usable email address that has not already been taken, though it helps to have an unusual name. In your new Gmail account, go to Configure Inbox in Settings (the cogwheel icon) and click the tab for Accounts and Import. This lets you import all the emails from your old Yahoo, Hotmail, AOL or other address.

Google uses an external service called ShuttleCloud to do this. It can take a few days or, in my case, more than a week.

Once you have all your emails in Gmail, set the old address to forward incoming emails to your Gmail inbox.

In Hotmail, go to the full Settings page, select Email and then Forwarding, and click the radio button next to “Start forwarding”. Next, go to “Forward my emails to:” and enter your new email address. Also tick the box that says “Keep a copy of forwarded messages” so that you can answer emails from either Gmail or Hotmail. In fact, you can add your Gmail address as a Hotmail alias, and add your Hotmail address as a Gmail alias.

Now you have a backup of all your emails online, and if you get locked out of one mailbox, you can use the other.

Mail transfers

Although it’s easy to get Gmail to fetch all your email from another service, this is not without problems. The main one for me was deleting thousands of emails to get inside Gmail’s storage limit. This is also not very practical because you start with a full mailbox.

Gmail makes a complete mess of tagging the incoming mail, and happily puts thousands of emails that you have filed away in folders – a good sign that you want to keep them – into the spam box. Not all of them, of course, just enough to be really annoying.

You also end up with long labels. First, every email gets tagged with the full email address of the old mailbox, which might be quite long (eg WolfgangAmadeusMozart@Yahoo.co.uk). Gmail doesn’t do folders or sub-folders, so it adds labels for the old folder names. That doesn’t leave much room for subject lines, so you may want to delete the email address label.

If you want to open a new mailbox to provide an online backup, it would be better to use Yahoo Mail, which is now owned by Verizon’s Oath division. Oath Inc also owns AOL, Tumblr, the Huffington Post, Weblogs and various other things.

Yahoo Mail provides 1TB of free storage space, so it swallows a full Gmail or Outlook.com mailbox and still leaves you with 98.5% free. You could use it to consolidate multiple accounts. The drawbacks are that Yahoo Mail no longer allows forwarding, and you have to agree to your information being shared with other Oath properties.

Personal domain names

One solution to the email address problem is to register your own domain. That way you can keep the same address for ever, as long as you remember to keep paying for it. If you owned, for example, mydomain.com then you could use myname@mydomain.com as your email address with any email service that will host it. If you don’t like the service, or it shuts down, you can switch to a different service.

There are three problems. First, domain names cost money. Second, it requires setting up. Third, Gmail and Outlook.com won’t host personal domain names as part of their free services. The only one that does, as far as I know, is Zoho. However, that only provides 5GB of storage and is web only: you can’t use a mail client such as Microsoft Outlook or Thunderbird.

Microsoft only supports personal domain names with Office 365 business accounts, so your best bet would be to sign up for Google’s G Suite. Prices start at £3.30 per month for 30GB of email storage, no adverts and, Google claims, “24/7 support”. Zoho Workplace offers the same features for $3 per month.

Have you got a question? Email it to Ask.Jack@theguardian.com