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Increase likelihood of email not being blocked

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I have a proposal solicitation application where I select typically 5 or so individuals and they get individual emails such as "Hello Bob, please click <here> if you wish to provide pricing for the following scope of work..."  It uses PHPmailer with a smtp gmail account.  The FROM name is my name, the FROM email is an email account associated with the application <bidding@bidsoliciationapp.com>, and the REPLY-TO name and email are both mine. 

A while back, individuals have told me that my emails often windup in their spam folder.

What might be causing this and what can be done to decrease its likelihood?

One potential culprit is all of the emails have a small footer with a disclaimer and a link back to a website, but the link utilized https which was no longer supported on the site and was broken.  Maybe related?

Thanks

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Unfortunately, there is no perfect answer. Every "spam" system can have different things it looks for to determine what is spam. If there was a simple list of things to do, then every spammer would do those things so their email would not wind up in spam. You will want to do some research, but here a a few things to consider:

1. The server sending the email should be an "authorized" sender for the domain in the from address. In this case you are using Gmail to send an email on behalf of 'bidsoliciationapp.com'. There are ways to change the MX records (similar to DNS records) to authorize a server for a particular domain. But, I think that would require reaction from Google as well if you want to use your current configuration. You may need to use a Google from address or use a dedicated emailing service that can help with the right configuration. Of course, that would cost money. I only understand these things tertiarily, so some of my 'facts' may be slightly off.

2. The name of the domain could be problematic with words such as "bids", "solicitation" could raise a red flag.

3. Content: I would not start with a "Hello Bob, please click <here> . . . " It just seems like something I would see in a Spam email. I don't know if that is part of the problem or not.

What you can do: Set up an account with a few different email providers and send some samples of your current emails to them to see if any are flagged as spam. If so, then change the content to something completely innocuous. Does that go through w/o being detected as Spam? If yes, then you know it is the content causing the detection. If not, then it is likely something to do with the configuration/meta data.

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Authorizing the servers involves setting up SPF records on the bidsoliciationapp.com domain which is something you should be able to do yourself.  Google has a help article detailing the configuration you need.

Setting up the SPF may or may not make a difference.  Spam filters are free to interpret a SPF lookup result with whatever weight they want compared to other factors, but having a positive response can only help.  Know that if you send email from places other than google using the same domain, you'll need to add those server addresses to your SPF record in addition to google's, otherwise they will become unauthorized and more likely to get rejected as spam.

Beyond that, as Psycho suggests the best thing you can do is just make sure the content of your messages doesn't look like it might be spam.  Avoid words/phrases commonly associated with spam if possible.

 

Fun anecdote:
GoDaddy's email servers used to flat out reject all my emails as spam.  I had a link to my personal website in my signature and at the time was hosting it on a home server.  Their spam filter scanned the links in the email, resolved the domains and check the IP against IP black lists.  Since it was a home server the IP of my domain was in a "Residential ISP" blacklist.   Apparently that single link was enough for their system to refuse delivery.   Removed the link and suddenly my stuff went through no problem.

 

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Thanks Psycho and kicken,

I will look into the authorized sender and also the spf records.  The domain in question is hosted by godaddy and I probably can use one of their email servers.

Yeah, "Hello Bob" does sound like something a spammer would say.  Do you think it is the name "Bob", whether I should be using "Hey" instead of "Hello", or something else :)  

Kicken, your fun anecdote sounds similar to my broken link, but maybe some of the filters have better memory now?

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