How to deal with Spam Issues and Gmail?

[apinto]

americanninja let's go by parts    (this is a long post, get ready!)

Thank you apinto! I will have to give that a try. I was worried about adding on software to the server after I got everything working with Sentora (i.e. in case it messes things up with Sentora and brings down the web server). Is it risky to do this? I'm assuming anything you install that's connected to the web server functions could cause trouble for Sentora, as Sentora is managing the server. Please let me know. 

Yes, every single change you make to the server you have some degree of risk of messing up the sentora environment.
The rule is always do a backup, I mean ALWAYS BACKUP.
You can never be too sure it will not break something.

As for the gmail greylisting, perhaps it's only the spammy emails that it's doing this? For example I just tested a few features on my drupal site which sends out emails to users based on things they do on the site. I have a test user on my Drupal site with one of my emails setup on my server. myemail@mydomain.com. I ran through and did a few things on the website that I know would trigger emails and those immediately came through to my gmail account (from my server via Drupal -> myemail@mydomain.com -> myemail@gmail.com). 

Probably yes (gmail spam filtering is a shady zone, it's hard to find facts about it  ).
My favorite Spam Checking tool is https://www.mail-tester.com/ (its easy to use and read the results, but probably there are better tools for more extensive usage), use this to check how your emails are being checked against SpamAssassin, SPF rules, DKIM, ReverseDNS etc. Consider a score above 8.5 to be good, anything above 9.5 is excelent;
However read all the diagnostics because even if SpamAssassin is not considering something critical, Gmail might!

These came through instantaneously, so no issues receiving them to gmail. And if I look at "mailq" now, I see nothing in the queue except that spam email which I posted above. So it seems gmail may just be delaying receiving this email?

Use the same tool to check your emails for spam, if they pass, you are ok to go  .

And it will keep doing this and eventually fall off of mailq's queue once it runs out of retries? Is this how these email servers work??

Postfix will retry multiple times or until he gets a permanent error, please read at least the first paragraph: http://jrs-s.net/2013/04/17/configuring-...n-postfix/ 

I'm a bit new to this. Obviously I think it will be a good idea to add the spam filter stuff to my server, but honestly I rather not mess around with the server unless I have to. I funnel all my email through to my gmail account and gmail does a great job of filtering the spam for me. So spam is no problem for me in terms of my inbox (which is why I funnel all my email to gmail in the first place). 

Appreciate any advice you can give. Thank you for the quick response!!

Never be afraid of experimenting (just don't experiment on production servers  ).
Everyone was new to everything at some point in their life, its only our persistence that makes us knowledgeable at any given topic; be persistent!


Regarding what you do (funneling all email through Gmail)  I also do the same (bye bye Outlook/Thunderbird ) and I've never got any issues, I even encourage my clients to do it.
You can even setup Gmail to check other servers using SMTP/POP or to send email using your own SMTP server instead of an alias (I guess oyu already knew this).

Going back to the "experimenting" with the server, well I STRONGLY encourage you to try Vagrant, it is possibly some learning curve to get your head around all the concepts of visualization but the documentations is really good and easy to follow if you are persistent.
Vagrant is a tool that allows you to "Create and configure lightweight, reproducible, and portable development environments." This means you can test what you wish on a virtual server at your local machine and "reset" in case something goes wrong, after you are comfortable you can update the production server safely knowing it won't break anything (still keep doing backup... we never know for sure...  )

You can check my topic about Sentora Vagrant Box (http://forums.sentora.org/showthread.php?tid=1476) that is a Ubuntu 14.04 x64 with Sentora default install.


If you still have issues with your email check the following thread about a user who had his email sent to spam on Gmail, Hotmail and Yahoo, but I believe it does not apply to your case however you can still check your IP reputation.

Make sure your ip is not blacklisted or with bad reputation.

Checking Senderbase (https://www.senderbase.org/lookup/?searc...38.182.138) does not look bad at all.

Are you sending to Gmail?
What is the reason gmail tells you for it going to spam? (please refer to: http://www.whatcounts.com/2012/03/gmail-...marketers/)

Does it only happens on Gmail?
One tool I found usefull is https://www.mail-tester.com/ , do a test and post back here the results url so we can check it better.

Try DKIM... might help...

Sometimes Gmail and Hotmail mark some IP ranges for unknown reasons (most related to previous owners spam reputation), when this happens there is little you can do, however I know of reports that sending email to multiple gmail address and marking the emails as "Not Spam" does help bringing your reputation back up (do this carefully or you might end up in a worse situation).