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Mike, Mac Medic
Category: Mac
Satisfied Customers: 8527
Experience:  Over 20 years IT experience with Apple computers in publishing, marketing and design.
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My name is ***** *****. I am getting the notorious error

Customer Question

Customer: Hi Mike, my name is ***** *****. I am getting the notorious error code 3253 when trying to send/receive to one of my pop emails. I should mention that this happens when using Outlook for Mac 2016. Also: using Apple Mail, it works find. In Outlook on Windows, I get a one-time (per session) popup informing me that the mail server's certificate is unknown. After I say OK, send/receive works fine.
JA: Thanks. Can you give me any more details about your issue?
Customer: I think everything would be fine if my Mac gave me the same prompt. It doesn't, though. It just loses the connection ... as if I had told it to not trust the certificate and not to ask again. How can I get that prompt again?
JA: OK got it. Last thing — JustAnswer charges a fee (generally around $36) to post your type of question to Mac Experts (you only pay if satisfied). There are a couple customers ahead of you. Are you willing to wait a bit?
Customer: I will need to leave in about 15 minutes unfortunately. I will wait until then.
JA: OK. Now I'm going to take you to a page to place a secure deposit with JustAnswer. Don't worry, this chat is saved. After that, we will finish helping you.
Submitted: 1 year ago.
Category: Mac
Expert:  Freddy M. replied 1 year ago.

Hello my name is***** do not rate until we are finished. I look forward to assisting and am very sorry to hear that you are having this problem. Does the Mac error ever mention a certificate issue as well?

Customer: replied 1 year ago.
Hi Freddy,
No, I wish it did, because then I could say: OK. If I could get that prompt to come up, I would probably be in business.
Expert:  Freddy M. replied 1 year ago.

Is there any more to the error other than the number 3523?

Customer: replied 1 year ago.
nope. but I think I just fixed the error myself. I examined the raw message source, found that the email server had a slightly different name (that the name I was using probably mapped to) and when I put that in, all of a sudden the last two weeks worth of email came in.
Expert:  Freddy M. replied 1 year ago.

Ok to be sure create a new email and send it to yourself. Let me know if you still get an error.

Customer: replied 1 year ago.
I did and it worked. My solution works in both directions.
Customer: replied 1 year ago.
Sorry, I really could have used a solution - which I am sure you would have found - a few hours ago. Meanwhile, I found my own.