Support Email notifications using port 465

[adefaria]

QuickDrop version

1.5.2

How are you running QuickDrop?

Docker (compose)

What happened?

I've been trying to set up email notifications with QuickDrop. Normally, I use my own cloud server on port 465 for secure email, but the email was failing. Actually, uploading a file was failing, and I initially thought that was because I was running QuickDrop in a Docker container on my Synology. My recent website redesign attempted to put QuickDrop in an <iframe>. Actually, the upload would work, but when it went to notify me, the email would time out. All I saw was "Upload failed, try again". The truth is, the upload worked, but the notification failed. The error message should distinguish between an upload failure and a notification failure.

So I asked Gemini about this, and we figured out that:

That is the problem.

Your screenshot confirms the Quickdrop settings UI is incomplete.

• Port 465 requires "Implicit SSL" (Encryption ON from the start).
• There is no checkbox for "Use SSL" (only "Use STARTTLS").
• Unchecking "Use STARTTLS" tells Quickdrop to use Plain Text (No security), because it doesn't know Port 465 is special.
• Sending Plain Text to Port 465 causes the Timeout (server waits for SSL, client waits for greeting).

The Solution: Use Port 587. Since the UI does have a "Use STARTTLS" checkbox, you must use the port designed for it.

Set SMTP Port to

1. 587
2. CHECK the "Use STARTTLS" box
3. Save.
4. Test.

This will work because both the client and server know how to start with plain text and then upgrade to encryption.

Steps to reproduce

1. Configure email on port 465
2. Send test email

Expected behavior

I expected the test email to be sent.

Logs / stack traces

Environment

No response

[RoastSlav]

Can you try the 1.6.0-dev build? you can pull it with the :develop tag.

[adefaria]

Works!