Sharper sends invoices, confirmations, statements, and other automated emails using an email address you connect from your own mailbox — not a generic Sharper address. This article walks through connecting that email address for the two most common setups, Microsoft 365 / Outlook and Gmail / Google Workspace (plus general guidance for any other provider), and how to confirm it's working with a test email.
All of this is managed at System Settings → Email Addresses. Access to this page depends on your user role — if you don't see it, ask your Sharper administrator.
Which Setup Do I Need?
Sharper connects to your mailbox one of two ways, and which one you use depends on your email provider:
Microsoft 365 / Outlook — connects using OAuth, a secure sign-in flow. You authorize Sharper by logging into Microsoft directly; Sharper never sees or stores your Microsoft password. Jump to the "Setting Up Microsoft 365" section for the steps.
Gmail, Google Workspace, or any other provider — connects using a standard username and password (SMTP). Jump to the "Setting Up Gmail / Google Workspace" or "Setting Up Any Other Provider" section for the steps.
Before You Start: The Email Address Screen
Navigate to System Settings → Email Addresses and open the email account you want to configure (or add a new one). Every setup uses these fields:
Field | What to Enter |
Display Name | The name customers see as the sender, e.g. "Sharper Marina Front Office." |
Email Address | The full mailbox address, e.g. [email protected]. |
User Name | Usually the same as the email address. |
Password | Only used for non-OAuth setups (Gmail, other providers). Not stored anywhere visible — if you change this mailbox's password with your provider, you must also update it here, or sending will fail. |
Outgoing Mail | Toggle on — this is what allows Sharper to send emails from this address. |
Setting Up Microsoft 365
Microsoft 365 (Outlook) mailboxes connect using OAuth instead of a password. If your Sharper implementation team already set this up for you, you'll only ever need the "Reconnecting / Re-Authorizing" section — the initial setup is normally done once by your Sharper implementation team, since it requires values from your organization's Microsoft admin (Azure/Entra) portal.
Initial Setup
On the email address screen, turn on the OAuth toggle.
Set Provider to Office 365.
In OAuth Configuration String, enter the connection details for your Microsoft account (
client_id,client_secret, andtenant). These come from your organization's Microsoft Entra (Azure AD) app registration — your IT administrator holds these values; if the app registration does not exist yet, it is created once as part of your Sharper implementation.Save the email address.
Reconnecting / Re-Authorizing
Do this any time Microsoft 365 sending stops working, or after your Microsoft account password or security settings change:
Go to System Settings → Email Addresses and open the Microsoft 365 email account.
Click Authorize.
A Microsoft sign-in window opens. Log in with this mailbox's Microsoft 365 credentials and approve the request.
Confirm the OAuth and Outgoing Mail toggles are both switched on.
Click Save.
Note: The Authorize button only appears after the email address has been saved once. If you're setting this up for the first time, save the record first, then reopen it to authorize.
The Email Addresses Authorization Screen
After you approve the request with Microsoft, you are returned to Sharper on a screen called Email Addresses Authorization. This screen exists only to finish the connection you just started — it is not somewhere you go on your own.
Select the Email Address the authorization belongs to.
Submit. You should see Authorization successfully completed, and Sharper returns you to that email address's record.
Finish this step in the same visit. The approval Microsoft hands back is single-use and short-lived, so navigating away and returning later means starting again from Authorize. If you land here and are not sure which address you were connecting, it is safe to leave and start the authorization again rather than guess — picking the wrong address connects the mailbox to the wrong sender.
Setting Up Gmail / Google Workspace
Gmail and Google Workspace connect using a standard username and password rather than OAuth. If you have 2-Step Verification turned on for the Google account (recommended, and often required by Google Workspace administrators), Google will not accept your normal account password for Sharper — you'll need to generate an App Password instead.
Generating a Google App Password
Sign in to the Google account you want Sharper to send from.
Go to your Google Account's Security settings and find App Passwords (search "App Passwords" if you don't see it listed — it only appears once 2-Step Verification is turned on).
Create a new app password (name it something like "Sharper").
Google displays a 16-character password. Copy it — you won't be able to view it again after leaving the page.
If your Google Workspace administrator has disabled App Passwords for your organization, ask them to either enable App Passwords for this mailbox or provide an alternative sending account. This is a Google account policy, not a Sharper setting.
Entering the Connection in Sharper
On the email address screen, leave OAuth off.
In Password, enter the App Password from Google (not your regular Google account password).
Turn on Outgoing Mail and set:
Outgoing Mail Server Address: smtp.gmail.com
Outgoing Mail Server Port: 587
Outgoing Mail Encryption: TLS/STARTTLS
Click Save.
Setting Up Any Other Provider
Any email provider that supports SMTP sending can be used — the settings just need to match what that provider requires. Turn on Outgoing Mail and enter:
Outgoing Mail Server Address — your provider's SMTP server (ask your IT team or provider's help documentation if you don't know it).
Outgoing Mail Server Port and Outgoing Mail Encryption — most providers use port 587 with TLS/STARTTLS, or port 465 with SSL. Use whichever your provider specifies.
User Name and Password — your mailbox credentials. Some providers (similar to Gmail) require a separate app-specific password when extra security like two-factor authentication is turned on.
Testing Your Setup
After saving your Microsoft 365, Gmail, or other provider setup, confirm it's working before relying on it for customer emails:
Create a small test reservation or invoice using your own email address as the customer.
Wait up to 10 minutes — delivery isn't always instant.
Go to Message Center and check the message's status:
Sent — Sharper successfully handed the email to your mail server. If you still don't see it in your inbox, check your spam/junk folder.
Failed — open the message to see the specific error returned by your email provider, and see the "If a Message Shows Failed" section.
If a Message Shows Failed
A Failed status in Message Center means your email server rejected the message. The most common causes are:
An outdated password (or, for Gmail, an app password that was revoked or regenerated)
A Microsoft 365 connection that needs to be re-authorized (see the "Reconnecting / Re-Authorizing" section)
An incorrect recipient email address
The recipient's mailbox being full or nonexistent
Spam or domain filtering blocking the message
Once you've corrected the underlying issue, you don't need to recreate the invoice or confirmation — go to Message Center → Failed, select the affected message(s), and use Resend to send them again. See Message Center - Resend for the full steps, including how to resend several messages at once.
For issues specific to one customer rather than your whole account (spam folder, incorrect address, etc.), see How-to Troubleshoot Customers Not Receiving Emails. If every email is failing, or nothing has sent since a specific date, the issue is with the connection itself — revisit the Microsoft 365, Gmail, or other provider setup steps rather than troubleshooting individual customers.