Autocomplete losing some (not all) addresses

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Outlook 2013 32 bit
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Hope someone out there can help with this, cos it's a strange one.

One of my users has a recurring problem where her autocomplete list will lose addresses seemingly randomly.
It does not lose all of the addresses, just some, and these are very often very frequently used addresses.
Today she complained that it has not retained an address of a recipient she mailed yesterday.
I haven't been able to find a pattern yet, although it does seem to affect mainly external mail addresses.

I have recreated her mailbox in Exchange, as well as her AD user account - problem persists. Created a new outlook profile - problem persists. Backed up the Autocomplete cache, cleared the it, imported a backup of it - problem persists. Cleared it and let her build it up again - problem persists.

I have used nk2info to check the store, at that point I discovered that there were 998 entries. A little research later revealed that Outlook 2013 only supports 1000 entries in the autocomplete list; I found a registry tweak to increase this, but it doesn't seem to help.

PC runs Win8 and Office 2013, connected to Exchange 2007 (SBS2008).

Has anyone seen this kind of thing before?

I have searched extensively but no-one seems to have had this kind of issue - there's the 'autocomplete is not working at all' issue (not relevant, cos it does work, mostly), and there's the 'autocomplete is suddenly empty' issue (also not relevant, cos it is not empty) but nothing like this that seems to be in between these two extremes.

Note - I know the Exchange is old, we will be upgrading it to either Exchange 2016 or going to Office 365 but that is a question of when the powers that be have made their decision. Either way, no-one else here has this problem, so I am disinclined to blame the age of the server for this.
The key to enlarge the list no longer works for newer versions- i think it only works for 2010. Is there any chance that the addresses are bouncing? Outlook (helpfully! :)) removes bouncing addresses from the list, even if they bounce for a dumb reason, like the mailbox is full.

Do any new addresses get written to the list and "stick" after restarting outlook or rebooting?
Unfortunately not. These are addresses that are in daily use - internal addresses now too, as she reported to me yesterday. In fact, it was my internal address that went missing yesterday.
When I found the list size restriction I reasoned that it might be overwriting entries in the list due to the maximum entries restriction.
One would assume that if this was the case, it would overwrite the least-frequently used entries first, though.
I applied the registry key and checked back a few days later to find the list was now sitting at 1023 entries, so it did appear to work in that regard, but alas, entries still disappear.
When I found the list size restriction I reasoned that it might be overwriting entries in the list due to the maximum entries restriction.
it will, but its supposed to overwrite the last used ones with the oldest dates... plus didn't you reset it, which would clear the file.

If only internal addresses are not saved, have the user select the contact from the global address list, not contacts. It might be happening due to how outlook cleans up bounced addresses - it's detecting the address the user choose is being redirected to the internal address so it removes the autocomplete entry.
Makes sense that it should overwrite the oldest/least used entries, but this is definitely not happening... Today again there was an instance of an address that she had been using this morning that was missing this afternoon. I'll manually remove some of the least commonly used addresses and see whether that that helps...
Today again there was an instance of an address that she had been using this morning that was missing this afternoon.
she was selecting it from the autocomplete list this morning? It really sounds like bounce removal behavior.

If she used the address and it either wasn't added to autocomplete or she restarted Outlook and it disappeared indicates file corruption. (You cleared the list by resetting it in Options?)

There are two places where there could be failure - the addresses are cached in the mailbox, written to the autocomplete stream file. (so new profile on its won won't do much.) It might be worth resetting the list in OWA then checking the mailbox using mfcmapi to verify the list cleared from cached mode.
This may not be a solution to your problem, but I suspect it could be useful for others out there, and I think Diane is one of the best and trustworthy resources for Outlook info available on the web so this is the place where posting my suggestion may do the most good.

Do the Autocomplete entries that go missing all belong to people found in the person's Contacts folder?

I helped a person who was not seeing an Autocomplete entry for their spouse. It turns out the spouse's Contact card "Display as:" field was set to show as "" instead of "FirstName LastName ("

When the "Display as" field was listing only the email address and the Outlook user typed in the proper FirstName of their spouse Autocomplete wouldn't suggest what the person expected as the first letter of the spouse's email nickname wasn't an alphabetical match for the actual given name that was being typed into the email address field.

The result being that after several characters were typed into the address field the remaining Proper Name (with email address) suggestions did not include the spouse's name. Which makes it appear to be missing, when it was actually filed by the email address and just not visible due to the alpha-numerically filtered Autocomplete suggestions.

After I updated the contact card "Display as:" field to be the spouse's proper name along with the email address, then Autocomplete worked as expected when typing in either the spouse's proper name or his email address.

Try typing in the 'missing' email address instead of the proper name. If the email address shows up then you know it is a problem with the "Display as" field in the person's Contacts.

If an email recipient is already in the Contacts folder then manually typing their proper name and address into the address field of a new email message (one of the fixes suggested above that didn't solve the problem) won't be remembered by Autocomplete no matter how many times you try. Outlook thinks it already knows the preferred way to list the person which is by using the exact text showing in the Contacts "Display as" field.
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