Forward your receipts into your books automatically, from Gmail or Outlook

Every Caribooks account has its own receiving address, something like a1b2c3d4e5f6@in.caribooks.com. Anything that arrives there lands in your document box, where it gets sorted to the right company and attached to the expense it documents. You will find your address on the Documents page of the portal.

Forwarding each receipt by hand works, and plenty of people do exactly that from their phone. This guide is about the other way: one rule in your mailbox, set up once, that sends receipts there without you touching them.

One thing to know before you start. A rule only catches mail that arrives after you create it. Nothing already sitting in your inbox will move, so it is worth forwarding the last month by hand once the rule is in place.

Gmail

Gmail will not forward anywhere until it has checked that the destination is real. It does that by emailing a confirmation to the address, which in this case is your own Caribooks address, so we see it and confirm it for you. You should not have to do anything. If your mailbox asks you for a confirmation code anyway, the portal shows it on the Documents page.

Do this on a computer. Gmail does not offer forwarding settings in its phone apps.

1. Open Gmail, then Settings, then See all settings, then the Forwarding and POP/IMAP tab.
2. Click Add a forwarding address, paste your Caribooks address, and confirm. Wait a few seconds for it to be verified.
3. Go back to the search box at the top and click Show search options.
4. Set the criteria. Use the From box, and list the senders you actually buy from, separated by OR: billing@acme.example OR receipts@telco.example OR no-reply@hosting.example. If you are not sure which addresses to list, search your own mailbox for invoice OR receipt OR facture and read the From column. Add vendors to the filter as you take them on.
5. Click Create filter, tick Forward it to, choose your Caribooks address, and click Create filter again.

Filter on the sender, not on has:attachment. An attachment filter is wrong in both directions at once. It sends us every client contract and holiday photo that happens to have a file on it, and it still misses the vendors who put the receipt in the body of the email with no file attached. Those body-only receipts work fine, by the way: Caribooks turns the message itself into a PDF and files that. They just have to be let through.

For the same reason, leave automatic forwarding of everything turned off. The filter is the better tool, because you decide exactly whose mail leaves your mailbox.

Two Gmail behaviours worth knowing. Gmail never forwards anything it has put in spam, so a misfiled receipt will silently never reach us. And for the first week Gmail shows a banner in your own inbox telling you your mail is being forwarded, which is expected and goes away on its own.

Outlook and Microsoft 365

Outlook has no confirmation step. You create a rule and it starts working, assuming your organization allows it, which is the part to watch.

1. Open Outlook on the web, then Settings, then Mail, then Rules.
2. Click Add new rule and name it something you will recognize later.
3. Add the From condition and enter your vendors' addresses. Avoid Has attachment: it lets far too much mail out and misses receipts written in the body of the message.
4. For the action, choose Redirect to and enter your Caribooks address.
5. Save.

Use Redirect to, not Forward to. It matters more than it sounds. A forwarded message arrives looking like it came from you, which destroys the one signal we use to tell which vendor a receipt belongs to and which of your companies it should be filed under. A redirected message keeps the original sender, so everything downstream works.

Check that it works

Forward one receipt to your Caribooks address by hand and watch it appear on the Documents page. That confirms the address and the intake.

The rule itself proves itself on the next invoice one of those vendors sends you. If a few days go by and nothing has arrived, read on.

When nothing comes back

On Microsoft 365, it is almost always your administrator. Microsoft turned off forwarding to outside addresses by default for organizations created from 2021 onward. Your rule still saves, still shows as enabled, and quietly does nothing. Worse, the bounce goes to whoever sent the original message rather than to you, so there is nothing in your own mailbox to find.

If that is what happened, your administrator needs to allow outbound forwarding for you. The setting lives in the Microsoft Defender portal, under Email & collaboration, Policies & rules, Threat policies, Anti-spam, then the outbound policy, where Forwarding rules has to be set to On. It can be scoped to a single person, so they do not have to open it up for the whole organization. Two other settings can block the same thing in the same silent way: remote domains, and mail flow rules.

On Gmail, there are three usual culprits. The filter points at the wrong address. The receipt landed in spam, which Gmail never forwards. Or your administrator has switched off automatic forwarding for the whole organization, in which case the forwarding options are missing from your Gmail settings entirely.

If you are stuck, write to support@caribooks.com and say which mailbox you use. The failure is usually one of the three above and takes a minute to spot.