In my endless endeavor to optimize my data storage scheme, I changed my Drobo 5D‘s drive redundancy setting from dual to single, such that I would only be able to sustain one drive failure, but I would gain an extra six terabytes of space. The free space has fallen below 20 percent, and I’ve ready reports of Drobos becoming incredibly slow once past three quarters full. I also had some issues connecting Drobo to Gmail, but got it working using Port 587 and checking the SSL box, despite this being against Google’s documentation.

I considered buying larger hard drives, but I should be saving my money right now. Most of what’s on the Drobo is already redundant with two 6TB hard drives I have inside my computer, though those are set up as a striped RAID array to appear as one fast volume, so they are pretty risky since either drive failing would make all the data inaccessible. But, all the rest of the data that isn’t on the striped drives is backed up to Backblaze.

After changing the Drobo from dual to single, initially nothing seemed to happen. I was expecting one of Drobo’s infamous 50,000 hour rebuild operations to get triggered, even though I knew technically that shouldn’t be necessary unless I was changing it from single redundancy mode to dual. After a few minutes, the free space reported jumped, and thankfully, no data reshuffling appeared to happen.

While I was in there, I turned on email notifications. I thought I’d done this before, but maybe that was on my last OS X installation.

Anyway, the point of this post is to say Drobo Dashboard 2.8.1 [80644] seems not to match Google’s official document, Google Apps SMTP settings to send mail from a printer, scanner, or app:

Configuration requirements

Port 465 (SSL required)
Port 587 (TLS required)

Requires authentication

Your full Gmail or Google Apps email address required for authentication

From that, I would think I need to set both Port 465 and SSL or set Port 587 but not SSL. In the Drobo Dashboard, I tried all four I found I could only get email to send with Port 587 and SSL. Maybe the developers meant the “SSL” setting to just mean “secure” and it actually does TLS in the background, but it seems confusing.

Settings combinations

Error: Port 465, SSL checked

First I tried using SSL with Port 465.

drobo_465_ssl_settings.png

That failed.

An error occurred while sending the test email. Cause: Interrupted.

Error: Port 465, SSL unchecked

I assumed Port 465 without SSL would not work also.

drobo_465_settings.png

Indeed.

An error occurred while sending the test email. Cause: Interrupted.

Error: Port 587, SSL unchecked

So I figured Drobo’s SSL wasn’t compatible with Gmail’s somehow, and I changed to Port 587 and left SSL disabled.

drobo_587_settings.png

That did not work either. Great.

An error occurred while sending the test email. Cause: SMTP protocol error: 530 5.7.0 Must issue a STARTTLS command first. y186sm28457116pfb.13 - gsmtp.

Success: Port 587, SSL checked

At this point I thought maybe Gmail wouldn’t work, and perhaps that’s why I didn’t have it set up in the first place like I thought I did. While I was at it, I tried Port 587 with SSL, which shouldn’t work.

drobo_587_ssl_settings.png

But it did.

You will receive a test email shortly. Please check your mailbox.

This makes me wonder whether the “SSL” checkbox actually makes it use SSL, or whether it uses either SSL or TLS depending on the port, and Drobo just didn’t label it very well. I suppose I could investigate and find out definitively, but for now I just want to document what worked.

Other possible issues

I checked to see if others ran into this issue, or perhaps I’m incompetent, or perhaps this is a new bug. I did find a thread on drobospace.com where people discussed issues when using Google’s two factor authentication:

RE: Having problems configuring email alerts. - danwcla***@gmail.com - 04-22-2014 08:33 PM

I finally got mine working by generating a GMail Application Specific password to use with Drobo. I’m using two factor authentication on my GMail, so it wouldn’t let me use my regular password.

That wasn’t my issue. Another person seems to have gotten it working with my exact settings above:

RE: Having problems configuring email alerts. - lilmill - 12-25-2013 03:23 PM

mine setup fine today, on both the new 5n and the fs i reset up my fs with new disk pack

here are my setups
to non gmail address
from xxx@gmail.com
mail server smtp.gmail.com
port 587

authentication
xxxx@gmail.com
password
use ssl

Another person quoted that reply and listed a bunch of combinations they tried unsuccessfully, though they don’t say explicitly they tried Port 587 with SSL, but they did check Google’s documentation also.

RE: Having problems configuring email alerts. - clindsay - 06-17-2015 04:00 PM

I have not been successful setting up alerts FROM a gmail account, either to that same gmail account OR to a hotmail account. I do not have access to a different SMTP server that does not require a username & password. I do not have google’s 2 factor authentication turned on.

I tried:

—> smtp.gmail.com & SMTP port = 25 without SSL
error: “STARTTLS required”

—> smtp.gmail.com & SMTP port = 25 with SSL
error: Protocol error 534 5.7.14 https://support.google.com/mail/answer/78754

—> smtp.gmail.com & SMTP port = 465 without SSL
error: timeout

—> smtp.gmail.com & SMTP port = 465 with SSL
error: timeout

Then I followed the instructions Google provides, on this page:
https://support.google.com/a/answer/176600?hl=en
for “restricted Gmail SMTP access” (TLS optional, apps can only send email to gmail accounts, etc.)

—> aspmx.l.google.com & SMTP port = 25 with SSL
error: Protocol error 534 5.7.14 https://support.google.com/mail/answer/78754

—> aspmx.l.google.com & SMTP port = 25 WITHOUT AUTHENTICATION
It worked!! Gmail filtered the email to spam, but OK.
It worked again!! Still filtering to spam, despite telling gmail this was NOT spam.
It failed on the third attempt in 20 minutes, generating an error message in Drobo Dashboard, like above. The error pointed to this page as explanation:
https://support.google.com/mail/answer/188131
which says, in sum, “The email you sent looks like spam, so we blocked it. Other email might not get blocked”.

Google recommends email generators, like Drobo email alerts, to follow these guidelines:
 https://support.google.com/mail/answer/81126?hl=en

Will Drobo’s developers update the Drobo Dashboard alerts to comply with Gmail’s requirements?

Another person wrote they had working settings that stopped working after changing a drive format, which should have nothing to do with email of course:

RE: Having problems configuring email alerts. - locksoft - 02-06-2016 09:26 AM

Update: Last night I switched from Ext2 to Ext4, so I reinitialized my 5N.
After that I wasn’t able to configure email anymore, even using the same, identical configuration.

Drobo guys, this is something you should indeed improve!

Let’s file this under “More reasons to distrust my Drobo”.