RoleSage email service
RoleSage can send candidate and application emails through the default RoleSage email service or, when connected, from a user's own Gmail or Microsoft 365 mailbox. The candidate/application timeline shows RoleSage-tracked communication history in one place.
Basic setup
Default sending needs no user setup. If no mailbox is connected, RoleSage sends the email through its system email service.
Hirers can connect Gmail or Microsoft 365 from account settings to send from their own inbox. Gmail is send-only in the first production release.
Connected mailbox mode is per account. One user's mailbox connection does not change how other users send email.
Mailbox connection can be disconnected at any time. After disconnecting, new emails return to RoleSage system sending.
Administrator setup
Operators should configure the system sender, inbound reply handling, the conversation reply-to domain, mailbox OAuth settings, and the support alert address through the normal application configuration and deployment settings. Do not hardcode provider credentials or support addresses in code.
Gmail and Microsoft 365 require provider OAuth applications before users can connect mailboxes. Until those provider apps exist, RoleSage continues to use the default system sending mode.
What happens when
No mailbox is connected
The email is sent by RoleSage. Replies are routed back to RoleSage using a conversation-specific reply address.
A mailbox is connected
The email is sent from the connected inbox and should appear in Sent Items. Gmail replies stay in Gmail for now; providers with read sync enabled can also sync replies into RoleSage.
A reply is received
RoleSage attaches the reply to the matching conversation using explicit thread or reply identifiers. Unmatched inbound mail is not guessed into a candidate timeline.
A safety check blocks the email
The email is not sent. The timeline records a failed send, the sender sees a clear blocked message, and support receives an alert for review.
Timeline and storage
RoleSage stores email conversations and messages against the owning account, with candidate and application identifiers attached to every communication record. That lets the current application timeline work now while keeping the model ready for a broader candidate communication history later.
Sent email, received replies, notes, delivery failures, and security-blocked sends can all appear in the communication timeline. A failed safety check is shown as a failed send, not as a successful email.
Security checks
Every RoleSage-originated email goes through a safety gateway before delivery. The gateway looks for unsafe web content, suspicious links, unusual link volume, links that point somewhere a recipient should not be asked to open, and attachment types that are commonly abused.
When a check fails, RoleSage blocks that send, records the failed attempt in the communication timeline, and alerts support without including full message bodies in the alert. Repeated unsafe attempts can temporarily pause RoleSage email sending for the account, then automatically clear after the safety cooldown.
Troubleshooting
Email shows as blocked: The email was not sent. Remove suspicious links, embedded content, or risky attachments, then try again. If the account is in a safety cooldown, wait for the cooldown to clear or copy the email to send from your own inbox.
Connected mailbox send fails: Reconnect the mailbox from account settings. If the problem continues, use RoleSage system sending while support reviews the mailbox connection.
Reply appears in email but not RoleSage: Confirm the original email was sent from RoleSage and wait for the next mailbox sync. Unrelated inbox messages are intentionally ignored.
Candidate did not receive an email: Check the timeline status first. If it says failed or blocked, it was not sent. If it says sent, check the recipient address and ask the candidate to check spam or quarantine.
Mailbox connection option is unavailable: Provider OAuth configuration may not be set up for the environment yet. RoleSage system sending should still work.