Why Some SteepleMate Emails Don’t Send from Your Church Gmail

Why Some SteepleMate Emails Don’t Send from Your Church Gmail

Why do some SteepleMate emails show SteepleMate/Pentesoft as the sender instead of our church email?

When you connect a church email account to SteepleMate, SteepleMate tries to send every message through that email account first using the secure app password you provide.

However, sometimes Gmail (for example) or the receiving mail server doesn’t accept the message. When that happens, the SteepleMate System uses a fallback sender (a SteepleMate/Pentesoft email address) so the email still goes out instead of being lost.

So when members see SteepleMate or Pentesoft as the sender, it usually means:

QuoteSteepleMate tried to send this as your church’s Gmail, but Gmail or the receiving server would not accept it. SteepleMate then resent it using its own sender so the message could still be delivered.

Info
SteepleMate is Powered by Pentesoft LLC. Learn more about Pentesoft at Pentesoft.com

When does SteepleMate use the fallback SteepleMate/Pentesoft sender?

A fallback can happen any time Gmail (or the receiving server) returns an error or refuses the message. Common categories:

  1. Gmail account or connection issues

    • The Gmail app password is invalid, revoked, or changed.

    • Security settings changed on the Gmail account (for example, 2-step verification or recovery changes) and Gmail starts blocking the connection.

    • Temporary connection problems between SteepleMate and Gmail (timeouts, network errors).

  2. Gmail sending limits reached

    • Standard @gmail.com accounts can send about 500 emails per day.

    • Google Workspace accounts can send about 2,000 emails per day per user.

    • If a church sends a lot of messages in a short period or to many recipients (especially via SMTP), Gmail may temporarily block further sending from that account.

  3. Gmail flags the message as risky or spammy

    • Message looks like bulk marketing (lots of recipients, certain keywords, link patterns, etc.).

    • Very high bounce rate or spam complaint history from that sender.

    • Attachments are too large or of a type Gmail doesn’t like.

  4. Recipient mailbox or server issues

    • Recipient mailbox is full or the account was deleted.

    • Recipient email server is down, overloaded, or temporarily refusing connections.

    • Greylisting or temporary deferral by the recipient’s mail system.

  5. Address or domain issues

    • Mistyped or invalid email address.

    • The receiving domain is misconfigured or has strict policies that cause more aggressive rejection of messages.


Whenever Gmail returns one of these types of errors, SteepleMate may decide:

Quote
We still need this message to go out, so let’s send it again using our own sending service.

That resend is what members see as “from SteepleMate/Pentesoft” instead of the church’s Gmail.


Can SteepleMate always tell us exactly why a specific email fell back?

Not automatically inside your admin view.

SteepleMate keeps system-wide delivery logs, but those logs include data for all churches, not only your church. For privacy and security reasons, that information isn’t exposed directly in your login.

However:

  • Our team can search the logs if you provide:

    • The recipient email address, and

    • Rough date/time (and which email it was, if possible).

  • We can then check the Gmail / delivery response and let you know what we’re able to see (for example, mailbox full, address invalid, sending limit reached, etc.).

In many cases, the bounce messages from mailer-daemon@googlemail.com already contain a short explanation — but the wording can be very technical or generic.


Can we stop SteepleMate from ever using the fallback sender and force it to only send from our church email?

For SteepleMate as it is today:

  • If the church’s email refuses or can’t send the message, SteepleMate has only two options:

    1. Use the fallback SteepleMate/Pentesoft sender, or

    2. Not send the message at all (let it fail).

From a system design standpoint, SteepleMate is choosing option #1 to avoid lost messages. That means there is no way to guarantee that every email will always show the church’s email address, because external systems (Gmail and the recipient’s server) can always reject or delay messages.


What can we do to reduce how often SteepleMate uses the fallback sender?

You can’t remove the possibility entirely, but you can reduce how often your emails are rejected.

Here are practical steps to recommend to churches:

  1. Stay within Gmail’s sending limits

    • Avoid large “email blasts” from a free @gmail.com account.

    • For heavier sending, consider a Google Workspace account, which has higher limits and is designed for organization mail.

  2. Keep mailing lists clean

    • Regularly remove:

    • High bounce rates hurt sender reputation and increase the odds that Gmail or recipients will refuse your messages.

  3. Encourage members to “trust” the church email

    • Ask members to:

      • Add the church email to their contacts.

      • Mark any messages in spam as “Not spam.”

    • This helps future messages land in the inbox.

  4. Keep content “church-friendly” and low-risk

    • Avoid “spammy” patterns: lots of ALL CAPS, too many links, strange attachments, etc.

    • Use clear subject lines (e.g., “This Sunday’s Service Details” rather than clickbait-style lines).

  5. Watch for Gmail security changes

    • If someone changes passwords, security settings, or 2-step verification on the church Gmail, you may need to update the app password used by SteepleMate.

    • If that app password no longer works, SteepleMate will increasingly have to lean on the fallback sender.

  6. Use a custom domain with proper authentication (when applicable)

    • For churches on Google Workspace using a custom domain (like office@churchname.org), make sure SPF, DKIM, and (ideally) DMARC are properly set up and passing. This helps Gmail and other providers trust the email.


Why do some fallback emails go to members’ spam/junk folders?

When SteepleMate uses its fallback sender, the email is effectively coming from a different “From” address and domain than the one members are used to.

Spam filters look at consistency (are messages coming from the same domain that recipients normally interact with?).

If members are used to seeing churchname@gmail.com and suddenly see something like notifications@pentesoft..., their email provider may treat it more cautiously at first, and that can lead to spam placement.

You can suggest that members:

  • Add the SteepleMate/Pentesoft sender to their contacts, or

  • Mark those messages as “Not spam” if they land there.

This helps train their mailbox that these fallback emails are safe and expected.


How should we explain this to our congregation or staff?

You can use language like:

Quote
Our church email is integrated with SteepleMate, which sends most messages directly from our church address. Occasionally, when Google can’t send a message (for example, due to limits or technical issues), SteepleMate uses a backup sender so your message isn’t lost. If you ever see a message from SteepleMate or Pentesoft, it’s still from us — it just used that backup path.

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