erik5763's profile

7 Messages


418 Points

Tuesday, January 24th, 2023 10:14 PM

My homestead/roundcube email account rejecting gmail email accounts and I keep getting a security certificate error when using Outlook

I have been using Outlook 365 for a long time now for email and routing my homestead email through it. As of about 6 months ago, I started getting a security certificate error everytime I opened outlook and every time I try to send an email with my roundcube homestead email account First with gmail email accounts, I keep getting a permanent error and rejection email for the last 3 weeks. I says the following address failed. Permanent Error due to authentication. Here is the verbiage:

host []

    SMTP error from remote mail server after end of data:

    550-5.7.26 This message does not pass authentication checks (SPF and DKIM both

    550-5.7.26 do not pass). SPF check for [] does not pass with

    550-5.7.26 ip: [].To best protect our users from spam, the message

    550-5.7.26 has been blocked. Please visit

    550-5.7.26 for more

    550 5.7.26 information. f5-20020ac87f05000000b003b3c56ce5b2si2800606qtk.367 - gsmtp

And then everytime I send an email for the last year, I get a security certificate error. Here is that error: It says the server you are connected to is using a security certificate that cannot be verified. The target principal name is incorrect. This is a pop up box that happens everytime I open up the email and when I send an email. I can click on the repair function in account settings and it fixes, but I'm not sure why. When I go into the advanced settings of Outlook. All settings are the same as before repaired Need help. Erik Mellenberg

Brand User

835 Messages


28K Points

6 days ago

Hi, I see you spoke with phone support. Were they able to help fully resolve the issue you were experiencing?

7 Messages


418 Points

@todd_h They were able to solve the issues! The gmail challenges needed to be done on homestead's end as the DNS codes were outdated and needed to be updated. This was taken care of while I was on the phone. And then Julia helped me out even further and we worked through the security certificate complications and took care of the that. So I am all set! Thanks! It turns out that my smtp and imap address was to my website as opposed to and It's crazy that for the last 6 months, I was receiving emails but just getting a security certificate error. Just glad it's taken care of ! You all are awesome!