My email triggers spam filters

Most of the email I send seems to get through just fine, but email I send to a couple of people at one corporate client consistently runs afoul of their spam filters. I've tried two different addresses: gmail and my personal domain.
However: I find that if I send email from either address *via the web interface,* it gets through immediately, no problem. But if I send using Apple Mail (latest Yosemite running on a Macbook Pro), my messages to these individuals are dumped into the spam bin. (In the case of one recipient, most messages get through, but not all. In the case of the other, very few messages sent via Apple Mail get through.)
I can't figure out why this is happening, and the recipients have tried working with their tech people on a resolution, to no avail. Does anyone have any advice or insight to offer? Thanks so much!
PS--Email sent from my iPhone using the same addresses (and to the same problem recipients) seems to get through without difficulty.

It does, though they are not configurable. As to any good, it's difficult to say unless you can check caught spam against uncaught spam, and spam will differ considerably from person to person.

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    Occam's Razor nearly always applies when troubleshooting technology issues!
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    Join our BBM Channels
    BSCF General Channel
    PIN: C0001B7B4   Display/Scan Bar Code
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