Front App Keeps Sending Emails to Spam: Why Whitelisting in Front Doesn't Work

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Home>Incident Reports>Front App Keeps Sending Emails to Spam: Why Whitelisting in Front Doesn't Work

Time to fix

5 minutes once we found the right layer

Incident

A title company's funding department opened a ticket: "In Front we are having an issue with it marking all of the wire confirmations that come from [a regional bank] as Spam. It does not matter if it is an incoming or outgoing wire or the amount. On each wire we are setting them to 'Unblock Sender' and 'Not Spam' but it will not help the issue." Every confirmation landed back in Spam.

Wire confirmations landing in Spam is not a small annoyance for a funding department — these are the emails that tell them a several-hundred-thousand-dollar wire actually went through. If one gets missed, a closing gets delayed. If one gets missed the wrong way, it becomes a fraud-risk conversation.

The funding manager flagged a useful breadcrumb: "I know there was an adjustment made when we had an issue with the wires with [a different bank] so not sure if that is somehow related." Same pattern, different bank.

Diagnostics

First check was the third-party mail hygiene layer in front of the mailbox. Nothing — messages were passing spam filtering cleanly at the MX layer. So the filtering wasn't happening at the gateway.

Next we tried Front's own settings. Added the sender as a Front contact. Added the bank as an "account" in Front. Specifically whitelisted the wire-confirmation sender. Told the user to run another test wire. It worked for about 48 hours. Then it broke again, same sender, back in Spam.

At that point the pattern was clear: whatever was marking these as spam wasn't respecting any of Front's own mechanisms, which pointed at the mailbox underneath.

How Front actually works with gmail

Here's the piece that catches people. Front is not a mail server. It's a shared-inbox client that syncs against an underlying mailbox — Gmail, Microsoft 365, whatever. Mail hits Gmail first, Gmail applies its filters and folders, and Front displays whatever Gmail did. Front's "Spam" folder in the UI is literally Gmail's Spam label.

So when you click "Not Spam" in Front, Front tells Gmail to remove the Spam label from that one message. Good. But Front has no mechanism to tell Gmail "never send mail from this sender to Spam in the first place." That rule lives in Gmail itself — in user filters or Google Workspace policies. Front's "Unblock Sender" is a Front-level concept that doesn't translate down to the Gmail filter layer. Every previous fix had worked temporarily because we were marking individual messages as not-spam after the fact, but Gmail's own learning kept categorizing the sender as spam on every new arrival.

We opened a support ticket with Front directly to rule out a Front-side whitelist we'd missed. Front confirmed the diagnosis: this was a Gmail classification issue, not something their platform could override.

Resolution

We added a Gmail filter on the specific mailbox Front was syncing to. The filter matched the bank's sender address and applied the "Never send to Spam" action:

1. Log into the Gmail account that Front is syncing (the actual underlying mailbox, not Front)
2. Settings → Filters and Blocked Addresses → Create a new filter
3. From: the exact sender address from the wire confirmations
4. Next → Check "Never send it to Spam"
5. Save

That's it. One filter, one mailbox, five minutes of work. The rule runs at Gmail's classification layer, which means by the time Front syncs the message, Gmail has already decided it's not spam, and Front displays it in the normal inbox.

Why in-front whitelisting doesn't stick

Worth spelling out because this is the exact trap. Front syncs against an external mailbox — it doesn't own the filtering rules. Clicking "Not Spam" reclassifies one message, not the sender. Clicking "Unblock Sender" is a Front-level policy invisible to Gmail. Front contacts and "accounts" affect Front's own metadata, not Gmail classification. Gmail keeps scoring each new inbound independently and keeps flagging the sender. The fix has to happen where the classification happens — for Gmail-backed Front, a Gmail filter; for M365-backed Front, a mail flow rule or tenant allow-list.

Outcome

After the Gmail filter went in, the funding manager sent two more wires that week. Both confirmations landed in the normal Front inbox. A few days later: "We have been getting the confirmations in Front again for that bank again and not in the Spam folder. I think the issue has been resolved."

As a bonus, we'd spent a few minutes while we were in there unsubscribing the mailbox from legitimate marketing lists that had accumulated in Spam — real unsubscribe links only, not the scammy stuff.

time to fix: 5 minutes
mailboxes touched: 1
wires recovered from Spam during troubleshooting: several
bonus marketing unsubscribes while cleaning up: a bunch

Key takeaways

Takeaway

Front is a client on top of Gmail (or M365), not its own mail server.

Takeaway

Front's "Not Spam" and "Unblock Sender" don't propagate to the underlying mailbox's filters.

Takeaway

if mail is landing in Spam persistently, the fix has to happen at the mailbox layer, not Front.

Takeaway

for Gmail: create a filter with "Never send to Spam" against the specific sender.

Takeaway

for M365: use a mail flow rule or tenant allow-list.

Takeaway

when a user reports "Front is doing X," check whether Front is actually doing X or just displaying what Gmail/M365 did.

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