Conversations FAQs

What file types can I attach in Conversations?

You can attach the following file types when messaging parents and families:

• Documents: .pdf, .docx, .doc, .csv, .xlsx, .xls, .txt, .pptx
• Images: .jpg, .jpeg, .png, .gif, .svg
• Video: .mp4, .mpeg
• Audio: .mp3, .wav, .wave, .aiff, .aif, .aifc, .gsm, .ulaw
• Contacts: .vcf, .vcard

This covers everything from enrollment forms and permission slips to photos from field trips.

Why do I get a "Delivery incomplete" error from Gmail when using BCC?

When you send emails from your synced email account using BCC addresses, Gmail might send you a "Delivery incomplete" error message. Don't worry — your email was likely delivered successfully and logged in Enrollio.

This happens because Enrollio uses BCC to log your emails automatically. Gmail doesn't receive a delivery receipt for the BCC address, so it sends the error even though everything worked correctly.

What to do: Check your Conversations inbox. If you see the email logged there, it was sent successfully and you can ignore the Gmail error.

Why can't I send Instagram DMs to people commenting on my posts?

Instagram's messaging rules require that a parent or prospective family send you at least one direct message within the last 24 hours before you can initiate a DM with them.

To reply to comments via DM: Use the "Instagram Interactive Messenger" action in your automations and set the reply type to "Reply to comment via DM." This lets you respond to post comments with a direct message, which can start a conversation thread.

This is an Instagram policy, not an Enrollio limitation — it helps prevent spam and ensures meaningful conversations with families.

[SCREENSHOT: Conversations inbox showing attachment options with supported file types highlighted] [SCREENSHOT: Email settings page showing BCC configuration for email logging] [SCREENSHOT: Automation builder showing Instagram Interactive Messenger action with reply type dropdown]