Outlook 2013 'safe' email marked incorrectly as spam/junk

DustSailor

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Hey everyone, I appreciate any help with this.

We're moving from one email server to another using google apps, all while using outlook 2013. During the transition (and after, if we can set it up), we have our old server forwarding email to our new email addresses. So old@oldmailserver.com forwards to new@newmailserver.com, and we now use new@newmailserver.com exclusively. Most email comes from our old account still.

For junk email, we block sender and the message is sent to the spam folder. We also set our @oldmailserver.com and things that aren't spam as 'safe senders' via outlook 2013 and remove them from the spam folder to inbox.

Yet for some unknown reason, some email that is forwarded from our old email addresses are still being marked as spam, even though they're on the safe senders list. Not all of them, just some. Like an email from account-security-noreply@account.microsoft.com was marked as spam, but not an email from Dusty@oldmailserver.com, yet both are forwarded from dusty@oldmailserver.com, and both are safe senders.

Any suggestions or further explainations on how this all works is greatly appreciated.
 

My Computer

System One

  • OS
    Windows 8.1 Pro with Media Center x64
    Computer type
    PC/Desktop
    System Manufacturer/Model
    Custom
    CPU
    Intel Core i7-3820 CPU OC @ 3.80GHz
    Motherboard
    Gigabyte G1.Assassin2
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    Main 500GB Hybrid Drive @ 7,200RPM
    Secondary OCZ SSD Vertex 3 Max IOPS
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    Silent Pro 1000w gold 80+
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    Azza Hurrican 2000
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    Microsoft Comfort Curve 2000
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    Tek Republic Wired Laser Mouse
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    Antivirus
    Defender, Malwarebytes
You may want to look at the junk/spam email's infobar to see how the email was routed to the "Junk E-mail" folder in Outlook 2013. Quote from this link:
Adding the address to the safe list may not prevent future messages from being moved to the junk mail folder, depending on what program moved the message. It could be a 3rd party anti-spam add-in or a rule in Rules Wizard.
 

My Computer

System One

  • OS
    Win 8.1
    Computer type
    PC/Desktop
    System Manufacturer/Model
    Dell Latitude
    CPU
    Intel i5-3350P (3.1 GHz)
    Motherboard
    Gigabyte
    Memory
    16 GBs
    Graphics Card(s)
    AMD Radeon HD7850
    Sound Card
    Built-in to MB
    Monitor(s) Displays
    2 x 24" Dell
    Screen Resolution
    3,840 x1,200
    Hard Drives
    128 GBs, OCZ Vertex, SATA III SSD
    256 GBs Intel SATA III SSD
    3 x Seagate 1 TBs HDD
    PSU
    Antec 750W
    Case
    Antec P185
    Internet Speed
    50 Gb/s
    Browser
    IE11, Firefox22.0
    Antivirus
    Vipre
    Other Info
    Works, most of the times unless Microsoft patches decide otherwise...
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