The problem
Your invoicing software is supposed to push invoices automatically after a job is signed off. It's not. So your admin team is manually raising invoices every week — and it's eating 6–8 hours of productive time.
This is one of those problems that's so normal it becomes invisible. "Yeah, invoices aren't syncing, but it's just how we work." Except it's not how it's supposed to work, and you're paying for a feature that's broken.
Why it breaks
Ninety percent of the time, it's one of three things:
1. An expired OAuth token
Your invoicing app (AroFlo, Zapier, Make, etc.) is supposed to stay connected to your accounting software (Xero, QuickBooks). The connection uses a security token that says "yes, I'm allowed to be here." The token expires, the connection dies silently, and invoices just... stop syncing. Nobody notices until someone runs a report.
2. A misconfigured integration setting
Someone set up the integration once, and a setting is slightly off — wrong tracking category, wrong account code, name/email mismatch. Everything else works, but just enough is broken that invoices don't land where they're supposed to, so the system gives up and stops trying.
3. A plan tier thing
Your plan doesn't include the add-on you thought it did. You upgraded your accounting software six months ago but didn't upgrade the invoice sync module. It worked until it didn't.
How to diagnose it (30 minutes)
- Check if the integration is still connected. Log in to both your invoicing app and accounting software. Look for Settings → Integrations or Connections. Is the status "Connected" or "Disconnected"? (If it's disconnected, re-authorise the connection using a login with admin permissions, and you might be done.)
- Call your invoicing vendor's support. Tell them: "Our invoices aren't syncing to [accounting software]. Can you audit our integration and check three things: (1) is the add-on included on our current plan, (2) is the OAuth token still valid, and (3) are the tracking categories and account codes still configured?" They have a 10-minute checklist for this.
- Check for name/email mismatches. In your invoicing app, do the contact names and emails match exactly with your accounting software? Trim spaces, check capitals. Mismatches are the #1 reason integrations work for some invoices but fail silently on others.
- Check your plan. What plan are you actually on? Not what you think you're on. Log in, go to Billing, and confirm. If you're on a plan from three years ago, that plan might not include the features you've been using. This is surprisingly common.
How to fix it (4 hours)
- Re-authorise the OAuth connection. If the token expired, log in to both systems with admin credentials and re-authorise. Save the connection. Test by pushing a single recent invoice manually and confirming it lands in your accounting software with the right line items and contact info.
- Fix any config issues. If tracking categories or account codes are wrong, the vendor support team can walk you through updating them. Re-test with a manual push.
- Run one week in parallel. Your admin team still raises invoices manually, but now they also check what the integration pushes automatically. Compare side-by-side. After one clean week, your admin team drops the manual process.
- Set a calendar reminder. Check the integration quarterly. It's boring, but it's how you stop this from happening silently again.
For a team of 3–5, that's one person per week of capacity you're getting back.
When to call someone
If after step 2 the integration is still broken, or if your vendor says you need to upgrade your plan to get the feature working, that's when you've got a business decision: upgrade, or live with the manual process. Either way, you've eliminated "nobody knows why it's broken."
The fix is never complicated. It's just invisible until you look.