When a buyer or artist says they never got the offer, contract or invoice, the useful first question is whether the problem sits inside Gigwell or out at a mail server. That one distinction decides everything you do next.
My email didn't arrive — where do I start?
Decide what "didn't arrive" means. Did the send throw an error on screen, or did it look like it went out and simply never landed? An error points at a setting inside Gigwell. A clean send that never landed points at deliverability.
Open the booking and read the recipient address exactly as it appears there, then check it against the address you expect. A stale or mistyped address is the single most common cause.
Look at the pattern:
Fails for everyone at one company — that company's mail server is filtering you. See the spam and bounce section below.
Fails for one address across several bookings — the contact record in Gigwell. See the articles on an artist member's email that won't save and an address that reverts to the old one.
Nothing at all happens when you click — your browser. See "Send Email does nothing."
Ask the recipient to check their spam and quarantine folders, and to allow-list your sending domain with their IT or mail provider.
Check whether the same address is sitting on both the buyer and the artist side of the booking. That blocks the send by design.
Check when the contact was added relative to the booking. Assistants and roster members are never applied backwards to bookings that already existed.
Ask yourself what changed recently — a new teammate, a contact sync, a hand-edited template, a cancelled seat.
Which side is which
Lives in Gigwell: the header, footer and signature wrapper, your sending domain configuration, contact records and their email mapping, e-signature sender identity, buyer and artist reply routing, and the message threads on a booking.
Lives on your side: your DNS records, spam filtering at your mail provider and at your recipient's, your browser's pop-up blocker and default mail handler, and any contacts synced in from an outside CRM or phone.
My emails are going to spam or bouncing
When Gigwell shows a send as successful but the message never lands — or comes back as a bounce — the message usually left Gigwell fine and was stopped by the recipient's own mail server. Filtering and quarantine decisions are made on their side, and no sender can override them.
Check whether the send showed as successful in Gigwell, or whether you saw an error on screen. An error means it never left; a clean send means it did.
Ask your recipient to check their spam and quarantine folders. Quarantined mail often never generates a notice, so they may not know it's there.
Ask your recipient, or their IT team, whether a bounce or rejection notice was generated. That notice usually says exactly why the message was refused.
Ask your recipient to allow-list your sending domain with their mail provider. That's the fix that sticks, and the one thing that reliably solves per-company filtering.
If you send from your own domain, confirm your SPF, DKIM and DMARC records are still published correctly at your DNS host. A record that was removed or edited will send your mail straight to spam.
Sending from your own authenticated domain gets filtered noticeably less than sending from a generic address. If you're seeing spam problems repeatedly, see the article on sending booking email from your own domain.
My invoice says Sent or Delivered but my buyer didn't receive it
Gigwell tracks invoice delivery separately from sending, so the invoice record tells you how far the email actually got: Sent, Delivered or Opened. Reading that status is the fastest way to work out where the problem is.
Open the booking, go to the Payments tab and open Invoices.
Click the invoice row and read the delivery status: Sent, Delivered or Opened.
Check with your buyer directly rather than looking for your own copy. If you copy yourself on invoices, your own mail server often drops that self-addressed copy — so not seeing it in your inbox doesn't mean your buyer didn't get it.
If your buyer genuinely didn't receive it, check the contact's email address on the booking. A typo in the buyer contact is the single most common cause.
Correct the email address if it's wrong, then send the invoice again from the invoice row.
Ask your buyer to check their spam and junk folders, and any shared accounts-payable inbox, before you send a third copy.
What the invoice statuses mean
Delivered means the receiving mail server accepted the message. It can still be filtered into spam or held by your buyer's security gateway after that point.
If the invoice is stuck on Sent and never moves to Delivered, the recipient address is the thing to look at first.
You can always download the invoice document from the attachments panel on the invoice and send it yourself as a stopgap while the delivery issue gets sorted.
If that doesn't work
If Gigwell itself showed an error, you can't tell whether the message ever left, or everything looks right on the booking and the message still never lands, this one needs our team. Start a chat from the messenger with the booking, the recipient address and roughly when you sent it, and we'll check the delivery record. For an invoice, also tell us which invoice it is and what the delivery status shows.
Good to know
Failing for everyone at one company points at that company's mail server. Failing for one address across several bookings points at the contact record in Gigwell instead.
Gigwell can't force delivery past another server's filters. Where the rejection is happening at your recipient's end, their IT or mail provider is the only one who can release it.
Fixing a Send Email button that does nothing
The Send Email action isn't a composer inside Gigwell. It passes the message to whatever mail program your computer or browser is set up to use. When nothing happens on screen, it's almost always because that request is being blocked, or because no mail program is set to receive it.
Get it opening again
Check whether a pop-up blocker is active in your browser. The request can look like a pop-up, so a blocker will stop it silently with no error. Allow pop-ups for Gigwell and try again.
Set a default mail handler. If you use webmail, your browser needs to know that — look in your browser's settings for handlers or protocol handlers, and set your webmail as the default for email links. Your webmail may also prompt you to allow this the first time you visit it.
Try a different browser. If it works there, the setting in the first browser is the thing to fix.
If you're on a work computer with managed settings, your IT team may need to allow the mail handler for you.
Good to know
Gigwell isn't a CRM and doesn't send free-form email outside a booking. Messaging lives in the Buyer and Artist tabs of a booking — that's where correspondence is sent and where replies thread back.
If you want the message sent and recorded inside Gigwell rather than from your own mail program, send it from the booking's Buyer or Artist tab instead of using Send Email.
Profile embed codes are meant for your website, not for email. Pasting one into a message won't render — it'll show as code or as nothing at all.
If the send goes out fine but never arrives, that's a delivery question rather than a browser one. See the article on where to start when an email doesn't arrive.
Fixing blocked images or attachments in messages
Sometimes a reply from a buyer or an artist arrives in the booking thread with its images or attachments showing as blocked placeholders instead of the actual files. There's no setting on your side causing this, and nothing you need to change.
Get the file another way
Check your own email inbox. Replies to a booking land in two places — the booking's message thread and the inbox of the person who sent the original message — and the copy that reaches your inbox usually has the attachment intact.
Download the file from there.
If you need it on the booking, attach it to the booking yourself so the rest of your team can see it.
If that doesn't work
If the attachment isn't in your inbox either, this one needs our team — start a chat from the messenger with the booking and roughly when the reply came in, and we'll take a look at what arrived.
Good to know
Ask your correspondent to resend the file if you need it quickly. A plain attachment on a fresh message usually comes through without any trouble.
Large files and certain file types are more likely to be stripped in transit. For riders, stage plots and contracts, a PDF is the safest format to ask for.
Blocked placeholders in the thread don't mean the message failed. The text of the reply is there and the correspondence is recorded — it's only the embedded content that didn't render.
Fixing the "cannot send to buyer and artist at the same time" error
This error means the same email address is sitting on both the buyer side and the artist side of the booking. Gigwell routes replies based on which side an address belongs to, so when one address is on both, it has no way to tell where a reply should land — and it blocks the send rather than guessing.
Find and remove the duplicate
Open the booking and go to the Buyer tab. Note every email address listed there.
Go to the Artist tab and note every address listed there.
Compare the two lists and find the address that appears on both.
Decide which side that address genuinely belongs on.
Remove it from the other side, then send again.
When the artist is your direct contact
Sometimes the same address is on both sides because the artist has no separate agent — you're dealing with the artist directly, and their address is the only one you have.
In that case:
Go to Settings → Roster and create the artist entity.
Add no member contacts to it. Leave the Members list empty.
On the booking, leave only the buyer address in place.
That clears the conflict and lets the documents go out.
Be aware of the trade-off before you do this: an artist entity with no member contacts gives the artist no visibility into the booking and no notifications of their own. Nothing reaches them through the platform — you'll need to forward documents to them yourself.
Good to know
If you want the artist to have their own visibility, the address on the artist side has to be different from the one on the buyer side. A second address at the same organisation is fine.
Adding a member to the roster entity later doesn't apply it to bookings that already exist. For those, open the booking, go to the Change tab, expand the arrows beside the artist entity, and add the member there.
If you have any questions or need additional help, please reach out to support@gigwell.com or use the chat widget on your screen.