Why am I getting a Hotmail SSL error and how do I fix it?

Email marketer from ServerFault explains that Server Name Indication (SNI) issues can cause SSL errors. SNI allows a server to host multiple SSL certificates on the same IP address. If the client does not support SNI, or if there's a misconfiguration, it can lead to SSL connection failures. He recommends ensuring that the client supports SNI and that the server is properly configured to handle SNI requests.

Email marketer from Stack Overflow suggests that an 'SSL handshake failed' error often occurs when the client and server cannot agree on a supported cipher suite. He recommends checking the server's supported cipher suites and ensuring the client supports at least one of them. Also, verifying that the server certificate is valid and trusted by the client is crucial.

Email marketer from Email Geeks recommends not using anything below TLS 1.1 anywhere.

Email marketer from SuperUser explains that using a self-signed SSL certificate can cause SSL errors with Hotmail. They advise using a certificate signed by a trusted Certificate Authority (CA). Hotmail and other major email providers typically do not trust self-signed certificates, leading to connection failures.

Email marketer from Reddit shares that Hotmail/Outlook often has strict SSL requirements. They advise ensuring that your sending server has a valid SSL certificate from a trusted CA. Additionally, they suggest checking if the server's IP address is blacklisted, as this can sometimes cause connection errors that manifest as SSL issues.

Email marketer from MXToolbox explains that an incorrect or missing reverse DNS (PTR) record can sometimes lead to SSL connection issues with email servers like Hotmail. They recommend ensuring that the sending server's IP address has a corresponding PTR record that resolves to the server's hostname. A missing or incorrect PTR record can cause the receiving server to distrust the connection.

Email marketer from EmailOnAcid recommends checking if your IP or domain is blacklisted if you are getting connection errors, as your reputation will effect deliverability.

Expert from Word to the Wise explains that outdated or insecure TLS configurations are a common cause of SSL errors with Hotmail. She emphasizes the importance of using current TLS versions (1.2 or 1.3) and disabling older protocols. Misconfigured cipher suites and a failure to adhere to modern security standards can also trigger these errors.

Expert from Email Geeks explains the cause of the SSL error is likely due to using an old and insecure TLS version. They suggest using TLS 1.1 as a bare minimum, and TLS 1.2 is better, as Microsoft might not accept older versions.

Expert from Spam Resource explains that issues with STARTTLS negotiation can result in SSL-related errors with Hotmail. He advises ensuring that the sending server correctly implements STARTTLS and properly negotiates the SSL/TLS connection after the STARTTLS command. Problems during this negotiation can lead to Hotmail rejecting the connection.

Documentation from Nartac Software explains the IIS Crypto tool for Windows Servers and describes that it can be used to enable TLS 1.2 and disable older, insecure protocols like SSLv3 and TLS 1.0. This can help resolve SSL errors by ensuring that the server supports modern, secure protocols required by services like Hotmail.

Documentation from OpenSSL explains that protocol version negotiation failures can lead to SSL errors. They advise ensuring that both the client and server have compatible TLS versions enabled. Specifically, disabling older, insecure protocols like SSLv3 and TLS 1.0 is recommended for security reasons, but ensure that the client and server both support a common, secure protocol like TLS 1.2 or 1.3.

Documentation from Microsoft Support explains that Hotmail/Outlook.com requires TLS 1.2 or higher for secure connections. SSLv3 and earlier TLS versions are deprecated. To fix SSL errors, ensure your email client or server supports and is configured to use TLS 1.2 or higher. Also, check for correct certificate installation and revocation status.

Documentation from Qualys SSL Labs explains that if an SSL certificate has been revoked, it can cause SSL connection errors. They suggest checking the certificate's revocation status using OCSP (Online Certificate Status Protocol) or CRL (Certificate Revocation List) to ensure that the certificate is still valid.