If your trip emails aren't going out from your Gmail, here's how to figure out why. Five things tend to be wrong, roughly in the order we see them. The fix for most is the same one-click Reconnect Gmail — symptoms tell you which.
1. The Gmail connection dropped
What you'll see. The Gmail card on Settings → Email integrations shows a gray Not connected pill. Your bell menu may have a notification that the connection between Trips and Gmail timed out, and recent trip emails went out from a Trips address instead of yours.
Why. Google invalidates the permission you granted to Trips after a security event (new device, password change, enrolling in 2-Step Verification) or a long idle period.
Fix. Click Connect Gmail, sign back in with the same Google account, and approve the send + read permission. Send a test trip message to yourself to confirm.
2. Your email did send — but from our backup sender
What you'll see. A recipient forwards you the email and the From reads something like Your Name <[email protected]> instead of [email protected]. Trips shows the message as Sent — it did go out, just not from your Gmail.
Why. Trips never just fails an email. If your Gmail isn't connected when we go to send, the message falls back to our backup sender so the client still hears from you — but we can't pretend to send from your domain without a connected mailbox.
From your Gmail (connected)
From shows
[email protected].Sent copy lives in your Gmail Sent folder.
Replies land in your Gmail inbox AND Trip Messages.
From the Trips fallback sender
From shows a Trips address with your name attached.
Nothing in your Gmail Sent folder.
Replies still route to Trip Messages via a special reply address.
Fix. Reconnect Gmail. Once the green Connected pill is back, every new trip email routes through your mailbox. Already-sent fallback emails stay as they are.
3. Your Workspace admin blocked the connection
What you'll see. You click Connect Gmail, Google asks you to sign in, then a Google screen reads "Access blocked: Your administrator has not allowed this app." You never make it back to Trips.
Why. Google Workspace admins can restrict which third-party apps employees may grant mailbox access to. Trips has to be on the approved list.
Fix. Forward this to your Workspace admin. They sign in to admin.google.com → Security → API controls → Manage Third-Party App Access and add UrTravelPro Trips as a Trusted app. Then click Connect Gmail again.
4. The send worked but replies aren't threading back
What you'll see. Your trip email went out from your Gmail. The client replied. The reply is in your Gmail inbox. But Trip Messages doesn't show it and no one gets a notification.
Why. Common causes: the client typed your address into To instead of hitting Reply (so the threading headers are missing), the original was a forward, or the reply landed in Promotions or a Gmail filter.
Fix. Confirm the client actually hit Reply. Check Promotions, Updates, and auto-archive filters. To get the reply on record, open the trip's Messages tab, click + New message, and paste the text as an internal note. If threading is broken for every client, that's on us — open a ticket.
5. You hit Gmail's daily sending limit
What you'll see. Trip emails show up as Failed with a rate-limit or quota error. Smaller batches work in the morning but fail by afternoon. The Gmail card stays green — that's the tell.
Why. Google caps how many emails a Gmail mailbox can send in a 24-hour rolling window — roughly 500/day for personal Gmail and 2,000/day for Workspace. Trips counts every recipient as one send.
Fix. Wait — the rolling window loosens automatically and sends resume the next morning. For big announcements use Marketing inside UrTravelPro instead; it's built for bulk and doesn't touch your Gmail quota.
Frequently asked questions
I just got a security alert from Google about Trips — is that legit?
Yes, expected after any Connect Gmail. Google emails a confirmation the moment you approve a third-party app; the app name reads something like UrTravelPro Trips. If you didn't just connect, click Check activity in Google's email and revoke if it wasn't you.
I belong to two agencies — do I connect Gmail twice?
No. The second agency's Settings → Email integrations shows a "Use a Gmail you already connected" shortcut. Click it and we wire the same mailbox in — no second Google sign-in.
Trips says Sent but the client never got it.
If Messages says Sent (not Failed), Gmail or our backup sender handed the message off. The next stop is the client's mail provider — spam, corporate filters, or a typo in their email are far more common than a Gmail issue.
Can I send from a Gmail alias?
Only if Gmail treats the alias as a Send mail as identity, and even then Gmail sends from your primary by default. Cleanest path: connect your real agency Gmail as the primary.
When to open a support ticket
Most Gmail issues solve themselves with a reconnect or a wait. Open a ticket when:
You reconnected, the pill is green, and trip emails are still going out from the backup sender.
Reply threading is broken for every client, not just one.
You get a Google error during Connect Gmail that doesn't match section 3.
The Gmail card shows refresh failures repeatedly within a day of reconnecting.
What to include: the Gmail address, whether it's personal or Workspace, a trip ID for one bad message, a screenshot of the Gmail card on Settings → Email integrations, and a forwarded copy of an email that showed the wrong From address.