Outlook 2010 sending safe senders email to junk box

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Outlook version
Outlook 2010 32 bit
Email Account
Recently a couple of my safe senders emails have ended up in the junk box. I have checked that they are marked as safe. I have Office 2010 Professional Plus installed. Did a search here and the information from what I could tell was quite old. This has not happened before and I have had this installed on the same computer for at least 2 years. Any help appreciated.
Was the entry on the the safe list identical to the email address on the message? Did you get a lot of mail in at once? If so, it can miss some filtering, although it usually is the opposite - leaving junk in the inbox.

Do you sync with a smartphone? Could it have junked the message?
Thanks Diane, the address's are identical to that shown on the safe senders and no I did not get a lot of emails at the time.
I do not synch with a smartphone.
Also I might add I use mailwasher pro and it has the senders marked as friends. Been working fine up until a week or so ago.
Do you know if it is it just these two that are affected? Any idea how many names are on the safe and blocked lists combined? There is a total limit on all 3 combined of approx. 2000 entries. (The exact # varies based on the length of each entry.) If you added more to any of the lists not long before you noticed it not working, then its possible the list is too large.
I think that there are about a dozen more from organisations that occasionally send stuff to me, but definitely no more. All up including safe senders and blocked, I have a tad less than 300 entries in both lists..
Definitely not oversized list if you only have 300. I'd probably export the list then reimport it. Also, make sure you have all office updates installed. Or see if any were installed around the time from your think it stopped working.

If there are windows updates waiting for a reboot, reboot asap. Outlook often acts buggy when there are updates waiting.
Ok saved it, then re imported it. All Office updates are current and no windows updates pending. We shall see what happens..thanks, I will let you know.
Just turned on my computer this morning, opened my mail, and nothing has changed, the two primary candidates emails were in my junk box yet again. So exporting and re-importing made no difference, back to the drawing boards hey!!
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