Connect your email

Connecting your mailbox does two things: emails you send to a client from the CRM go out from your real address, and their reply comes back into Conversations — attached to the client’s record — instead of disappearing into a personal inbox nobody else can see.

This is a per-user, day-one job. Everyone on the account connects their own mailbox.

Email in your CRM is two separate jobs

Most of the confusion around email setup comes from mixing these up. They are not the same setting, they don’t live in the same place, and doing one does not do the other.

	Your personal mailbox (this article)	Your sending domain (separate article)
What it is	Your own Gmail or Outlook account, linked to your user profile	Your domain, authenticated so bulk email is trusted
What it powers	One-to-one emails you type and send to a client	Automation emails, appointment reminders, bulk sends
Where it lives	Settings → My Profile	Settings → Email Services
Who does it	Each user, for themselves	Once, for the account
Time	About 5 minutes	30 minutes plus DNS wait time

The short version: connecting your mailbox fixes your personal email. It does not fix deliverability for automated or bulk email. More on that below — it’s the single most common misunderstanding, and it’s why people end up in spam folders wondering what went wrong.

Before you start

• The mailbox you actually want to use. Connect the address you already email clients from — the one they recognize. Not a throwaway.
• Gmail or Outlook. Those are the two supported providers. If your email runs on something else, reach out and we’ll sort out the right approach with you.
• If your email is on a company Microsoft 365 account, your IT admin may block third-party apps by default. Worth knowing before you hit a wall mid-setup.

Connect your mailbox

1. Open Settings from the left menu.
2. Go to My Profile.
3. Scroll to the Email (2-way sync) section. Two-way sync just means email flows both directions: what you send from the CRM shows up in your mailbox’s Sent folder, and what a client sends back shows up in Conversations.
4. Choose Gmail or Outlook, then click Connect.
5. Sign in at the Google or Microsoft screen that pops up. You’re signing in with your provider directly — the CRM never stores your email password.
6. Approve every permission it asks for. This is where most setups break. The connection needs permission to read and send on your behalf. If you decline any part of it, the connection will look like it worked and then quietly fail later.

When it’s done, your address appears in that section marked as connected, with a pen icon to edit it and a trash icon to remove it. That’s the same place you’ll come back to if the connection ever needs re-authorizing.

Pick the address you’ll still be using in two years

Your connected address becomes the “from” address on every one-to-one email you send from the CRM. Changing it later means clients see a new sender. Choose once, deliberately.

What actually syncs — and what doesn’t

Knowing the boundaries here saves you from thinking something is broken when it’s working as designed.

Syncs, on both Gmail and Outlook:

• Emails you send to a contact from the CRM. The thread — and everything that follows in it — stays in sync between Conversations and your mailbox, including a copy in your Sent folder.

• The client’s replies to that thread, from either side.

• Inbound email a client sends you out of the blue. If someone already in Contacts emails your connected address, that message flows into Conversations on their record — even if you never emailed them from the CRM first. A thread can start from either end. This works the same way on Gmail and on Outlook.

Doesn’t sync, on either provider:

• Your email history from before you connected. The sync starts the day you turn it on. It will not backfill old conversations.
• Email from people who aren’t in Contacts. The sync routes a message by matching the sender to a contact record. Mail from an address with no matching record has nowhere to land. Add them to Contacts first, or send them the first message from the CRM, which links the thread for you.
• Email from a teammate who is also a user on your account. If someone is both a contact and a user, their email is deliberately excluded from the sync — it may contain internal information. This is by design, not a bug.
• Automation and bulk emails. These keep sending through the account’s email service, not your personal mailbox. That’s by design too — and it’s the next section.

Attachment limits

The limits differ by provider, so check the column that applies to you.

	Gmail sync	Outlook sync
Size limit	Up to 25 MB	Up to 3 MB
Over the limit	The email composer caps attachments at 20 MB — anything bigger is uploaded automatically and sent as a clickable link instead of a file	The message won’t make it into the synced thread
File types	No type restriction is published	Documented as: JPG, JPEG, PNG, MP4, MPEG, ZIP, RAR, PDF, DOC, DOCX, TXT

What this means in practice

On Gmail, you’ll hit the composer’s 20 MB ceiling before you ever hit the 25 MB sync limit — and that’s fine, because oversized files are turned into links automatically rather than dropped. There’s no published file-type restriction to worry about.

On Outlook, the 3 MB ceiling is genuinely small — a few photos of a signed document will blow right past it. If an attachment doesn’t make it into the synced thread, that size limit is the first thing to check. Send a PDF or a secure link instead.

Prove it works

Don’t assume. Run this test, which takes two minutes:

1. Create a test contact with a personal email address you control (call it “Jane Sample”).
2. Open the contact, go to Conversations, and send that contact a short email from the CRM.
3. Check three things:
   • It arrived, and the “from” address is your connected mailbox — not a generic address.
   • A copy is sitting in your mailbox’s Sent folder.
   • When you reply from that other address, the reply appears in Conversations on Jane Sample’s record.

If all three are true, you’re connected. If the reply lands in your regular inbox but never appears in Conversations, the sync isn’t fully authorized — see troubleshooting below.

What this does not fix: bulk email and spam

Here is the honest part. Connecting Gmail or Outlook makes your personal email work. It does nothing for the emails your CRM sends on its own — appointment confirmations, reminders, post-sale follow-up sequences, and any bulk send to a list. Those go out through the account’s email service using your sending domain, and inbox providers judge them on entirely different criteria.

If your sending domain isn’t authenticated — proven to be really yours, via a few DNS records at your domain registrar — those automated emails land in spam no matter how well your personal mailbox is connected. That setup is its own job, and it’s the difference between reminders that arrive and reminders nobody sees.

Set up a sending domain if you plan to:

• Send appointment reminders or automated follow-up (that’s most people on day one)
• Email your whole client list in bulk: newsletters, seasonal outreach, announcements
• Stop landing in spam

→ Set up your sending domain

Your personal mailbox is not a bulk sending tool

A standard Gmail account caps out around 500 messages a day, and Google and Microsoft both throttle or suspend accounts that behave like mass senders. Don’t try to route a campaign through your personal mailbox — you’ll get your mailbox limited and your list will still land in spam. Bulk email goes through the sending domain. That’s what it’s for.

Troubleshooting

Symptom: “Insufficient permission” error, or sync just stops working. Why: The authorization expired or was revoked — usually after you changed your email password, your company updated its security policy, or a permission got skipped during setup. Fix: Reconnect the mailbox from Settings → My Profile → Email (2-way sync). Click the trash icon next to the connected address to remove it, then connect it again and approve every permission on the consent screen. (The pen icon edits the connection; the trash icon removes it.) If it still fails, revoke the CRM’s access from inside your Google or Microsoft account security settings first, so the next attempt requests fresh permissions from scratch. Reconnecting in a private/incognito browser window clears up stubborn cases where the browser keeps signing you in as the wrong account.

Your mailbox lives in My Profile, not Email Services

Personal mailbox connections are managed only under My Profile — that’s where you connect them, edit them, and remove them. Email Services is the account-level sending domain, a different job entirely. If you’re hunting for a disconnect button, you’re looking for it in My Profile.

Symptom: A client emailed you directly and it never appeared in Conversations. Why: Start by checking whether the sender is a saved contact — then the answer depends on your provider.

• Not in Contacts: the sync has no record to attach the message to. Working as designed. Add them to Contacts, or send them the first message from the CRM, and their email will flow in from then on.
• A teammate who is also a user on your account: those emails are excluded on purpose. Working as designed — don’t chase it.
• A saved contact, on either Gmail or Outlook: this is a real fault, not expected behavior. Inbound email from a saved contact should sync whether or not you emailed them from the CRM first. Do not explain this one away. Fix: remove and reconnect your mailbox using the steps above, approving every permission. If it still doesn’t sync, reach out.

Symptom: You connected Outlook, but nothing syncs at all — or the Outlook option won’t complete. Why: Business Microsoft 365 tenants often require each user to individually consent to third-party apps, and some tenants block them outright at the admin level. Admin approval elsewhere in the org doesn’t automatically cover you. Fix: Run the connection again and accept the full permission list. If Microsoft refuses or the screen never appears, your IT admin needs to allow the app for your account. If the Outlook option isn’t showing up in your profile at all, contact us — that’s on our side to enable, not yours.

Symptom: You sent an email with an attachment and it never appeared in the thread. Why: Size is the usual culprit, and the ceiling is much lower on Outlook — 3 MB there, versus 25 MB on Gmail. Fix: Shrink it and re-send: compress the file, export it to PDF, or skip the attachment and send a secure link. See Attachment limits above. If a comfortably-sized attachment still doesn’t come through, reach out and we’ll look at it with you.

Symptom: Automated reminders and follow-ups are landing in spam, even though your personal test email arrived fine. Why: These are two different sending paths. Your test used your connected mailbox; the automation used the account’s sending domain, which is probably unauthenticated. Fix: Set up your sending domain — full walkthrough here. This is the fix. Nothing you change in My Profile will affect it.

Symptom: The wrong address shows in the “from” field when you email a contact. Why: Either no mailbox is connected on your user profile, or you connected a different address than you expected. Fix: Check Settings → My Profile → Email (2-way sync) and confirm the connected address is the one you want clients to see. If you’re logged in as a teammate or a shared login, you’ll be looking at their profile — the mailbox connection is per user, not per account.

Keep client health information in secure channels

Email is a client-communication tool, not a place for protected health information. Keep policy numbers, diagnoses, and health details out of subject lines and message bodies, and use the platform’s secure channels for anything sensitive. Anything you send from the CRM also lives in your connected mailbox — so treat that mailbox as part of your security surface, and lock it with a strong password and two-factor authentication.

Next step

If you’ll be sending appointment reminders, automated follow-up, or any bulk email — and you will — do this next: Set up your sending domain.

Otherwise, keep moving through setup: Set up your phone and texting.