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The question really says all about what I want to do, or need help on. I recently signed up for a new outlook account to try out the new outlook preview and I've set up gmail to automatically forward new messages to my outlook account so that I can use outlook to manage my gmail account.

Do any of you know how I would be able to forward the old messages, and not the new ones, to my outlook? I already know that they can be fetched into outlook by outlook's very own service, forwarding would be faster, so..?! Also, since I now use outlook to send email on behalf of my gmail account, how do I make it sync each email I send using outlook with my gmail - so that gmail has it all?

TY in advance. Please do help.

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How many emails? Presumably Outlook is able to fetch by POP3 (is that the service you are talking about?) I would have thought this would be the preferred way to get all past and future emails are available Outlook. Do you want sent emails from Outlook to appear as "sent" emails in Gmail, or are you OK with them just being stored in your Inbox? – w3d Sep 2 '12 at 9:59
@w3d - More than 3000 emails. Outlook was able to fetch by POP3, but some messages weren't fetched(10-20) and many that were aren't searchable properly. For example, there is one really old email - which I when I search in gmail with the from: address, it's located instantly. However, in outlook, I have to specify that a file was attached with it, that it has x keywords and only then can it locate it. However, it's not the same with the newer(and old) emails. And yes, I want sent emails from Outlook to appear as "sent" in gmail. Hope I made myself clear. TY! – alvasrawuther Sep 3 '12 at 9:34
I'm not sure why POP3 didn't work 100% for you. I would have said this was some kind of deficiency with Outlook, but I'm not sure. Is POP3 set for all mail in Gmail, and not just since it was enabled? If the email has already been retrieved by Outlook then why wouldn't it be able to find/search it? "Forwarded" emails will have different SMTP headers to emails fetched via POP3, so your searching abilities would be again affected. Are you able to connect to Gmail using IMAP, from Outlook? IMAP would be the only way to sync sent items - IMHO. – w3d Sep 3 '12 at 12:18
@w3d - When I checked, POP3 was not set for all email, but I just enabled for all. Should I delete all mail that was previously downloaded to Outlook and try again? When it comes to search it can locate it but I have to specify the details, unlike in gmail when only one detail, like the from: address is enough. When I just enter the from: address for search in outlook, it shows no emails at all. Forwarded emails will have different SMTP headers, but then why would that affect search? How do I connect to gmail with IMAP using outlook? The new outlook doesn't support IMAP, but EAS. – alvasrawuther Sep 3 '12 at 16:29
IMHO, I would not delete previously downloaded POP3 email - if you want to keep it. POP3 download is usually a one off, if you subsequently delete it, Outlook might not refetch it (or Gmail will know that you've already fetched it?). Does Outlook use the "from:" search operator in the same way as Gmail? Different SMTP headers potentially means different "From:", "To:" headers etc. – w3d Sep 3 '12 at 17:15
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