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Every few days, Outlook asks for my password, and I give it and check the "Remember me" box. After a few days - I should maybe not how many; if it's regular or ranmdom - it has forgotten me, and I must repeat the password entry.

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Reset to default
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Have you tried setting your profile as default in the mail profile? You can achieve this by: Control panel > User accounts > Mail > Show profile and then setting yours as default. If it is not in there you can just add it and set as default. Hope this helps.

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