Can replies go to a different address, and can the Inbox "Open" button use my own mail app?

Two asks that tend to arrive together once outreach is really running. The first: Send out cold emails via one email address and have the reply to email be a different address. The second: when I tap "Open" on any of the things that need my attention, it opens up Microsoft 365 (outlook.cloud.microsoft) for me. I'd rather have it open Apple Mail for me if possible. Both are fair. Neither has a setting in Booked Solid today, and this article says that plainly rather than leaving you hunting through Settings for a switch that is not there. Here is what the app actually does in each case, and the nearest real path to what you wanted.

The short version

• There is no separate Reply-To field. Outreach goes out under the connected account you send it from, and replies come back to that same address. The fix is to send from the address you want the replies in.
• The Inbox Open button opens the original message's web link in your default browser. For a Microsoft 365 connection that is Outlook on the web, at outlook.cloud.microsoft. There is no setting to make it open in Apple Mail, and none that hands the message to your operating system's default mail client.

Sending from one address and getting replies at another

Outreach in Booked Solid goes out through your own connected email account, set up under Connections > Mail & calendars, under the address whose purpose tag fits the job. An account on that form carries a name, a purpose tag (bookings, personal, support or business), its email address, its mail servers and its sign-in. There is no Reply-To box on it, and there is no global one in Settings. When the app writes an outgoing message it fills in the From, To, Cc and Subject lines, and nothing in there splits the reply address away from the sending address, so a message that goes out from outreach@yourdomain.com comes back to outreach@yourdomain.com.

The account form holds no advanced section with that field tucked inside it either. Skip that search.

Send from the address you want the replies in

The workaround is not really a compromise. It is the setup we would have pointed you at anyway: add the address you actually want replies to land in as its own account, and run the outreach from that one.

1. Open the Connections tab and find Mail & calendars at the top.
2. Under Email accounts, click Add an email account.
3. Give it a name you will recognize, then set its purpose tag. Tag it bookings if this is the address gig replies should land in. Do not tag it personal: mail on a personal account is deliberately kept private and is never filed into the Inbox.
4. Choose how it connects. Any email (IMAP) is the default and the one that works with a provider-issued app password.
5. Save it, then use Check it on that account to confirm the app can really reach it before you send anything from it.

Now the sending address and the reply address are the same address by design, which is the outcome you were after. It is also the healthier arrangement: sending from a real mailbox that genuinely receives, at a human pace, is a large part of why this kind of outreach lands at all. The article Cold outreach in Booked Solid: what's built in (and what isn't) makes the same argument at more length.

If your mail provider has a reply-to setting of its own, that is a provider feature and not a Booked Solid one. The app writes the message with a From line and no Reply-To line; what your provider does with it on the way out is between you and them. Send one message to an address you control and watch where the reply actually goes before you build a campaign on it.

One caveat if both addresses are Microsoft 365 mailboxes: the Microsoft 365 (Outlook, Teams) card under Connections > Tool access (optional) holds one Microsoft sign-in at a time. Signing a second account in there replaces the first rather than adding to it. Two Microsoft 365 mailboxes connected side by side is not something this version does.

Where the Inbox Open button actually takes you

An Inbox item can carry a link back to the original message, captured at the moment the app took that message in. A message from a Microsoft 365 connection carries one, because Microsoft hands the app that message's own address in Outlook on the web, which today lives on outlook.cloud.microsoft. The Open button hands that link to your operating system, and because it is a web address, your operating system does with it what it does with every web address: it opens your default browser. That is the whole mechanism, and it is why you land in Microsoft 365 instead of in your mail app.

No setting changes this. Nothing on the Inbox item, nothing on the connection and nothing in Settings will make Open open Apple Mail for you, or point it at your operating system's default mail client. Do not spend an evening looking for it.

The dead end: swapping your connection to change where Open lands

The natural next move is to turn the Microsoft 365 connection off and add the mailbox again as Mail app on this computer, on the theory that the Inbox will then hand you over to Apple Mail. That is a dead end, and it can burn an afternoon.

The app does find your Apple Mail. It then tells you the truth: "Found a mail app for you@yourdomain.com, but Booked Solid cannot read it yet. Choose IMAP and use a provider-issued app password for background inbox listening." Reading straight out of the Apple Mail app is not something Booked Solid can do yet, so that route ends by pushing you back toward an app password, which is the very thing most Microsoft 365 users chose the Microsoft sign-in to avoid. If your mail lives in the Microsoft 365 cloud, the Microsoft 365 sign-in is the correct connection, and turning it off does not change what the Open button does. Leave it on.

What to do instead: write the reply in Apple Mail

1. Find the conversation in the Inbox.
2. If the drafted reply is not quite in your voice, click Edit, make your changes, and click Save.
3. Click Open & copy. Your reply goes to the clipboard and the web view opens, which you can close. The line that appears under the buttons says which of the two actually happened; if it asks you to copy the reply yourself, copy it from the draft block above.
4. Switch to Apple Mail, open the same message there, paste your reply and send it yourself.
5. Come back to Booked Solid and click I sent it.

That last step is not paperwork for its own sake. Booked Solid never marks a conversation as replied unless you confirm it, which is what keeps the digest honest about what actually happened. Skip the confirmation and the same conversation keeps sitting there asking for your attention.

Both of these are worth asking for

A Reply-To address on an outreach account, and an Open button that honors your operating system's default mail client. Neither exists today, and neither is an unreasonable thing to want. If you need one of them, reply on your ticket saying which one and what you would use it for, and it goes in front of the team as a real feature request.

If it still does not work

If the trouble is not where replies land but where the outreach came from, that is a different fault: check which account carries the bookings purpose tag under Connections > Mail & calendars, and run Check it on it to see whether the app can reach that mailbox at all.

If an Inbox item shows no Open button, that item has no web link back to an original message, and there is nothing to fix. Microsoft 365 supplies one; a mailbox read over IMAP or POP3 does not, and neither does a conversation you dropped in by hand. It is not a fault to chase.

Still stuck? Submit a ticket from this help center and we'll take it from there.