Briggs Softworks

Using Office 365 smtp with Secure Connection and get this error...

Email failure (Error connecting with SSL.
error:1408F10B:SSL routines:SSL3_GET_RECORD:wrong version number) sending password change code to

Do you have the OpenSSL DLL files in the program folder? I have links to those in the FAQ at http://www.briggsoft.com/pmfaq.htm

Yes the OpenSSL DLL's are in the folder.

I've always used gmail's server for smtp. Are you using smtp.office365.com for the server and 587 for the port? Does it work with "secure connection" turned off?

Secure Enabled Error:

2020-03-27 11:07:20|Email failure (Error connecting with SSL.
error:1408F10B:SSL routines:SSL3_GET_RECORD:wrong version number) sending password change code to


Secure Disabled Error:

2020-03-27 11:11:11|Email failure (SMTP; Client was not authenticated to send anonymous mail during MAIL FROM [YTXPR0101CA0027.CANPRD01.PROD.OUTLOOK.COM]
) sending password change code to

It still sounds like out-of-date OpenSSL files to me but I don't use Office 365. I'd suggest just getting a gmail account and follow the instructions at http://www.briggsoft.com/pmfaq.htm (item 6).

Also, please make sure you try using the 32 bit SSL files first. I assumed I had to use 64 bit files. And I was running into the same issue you were. I instead used the 32 bit files, and it fired right up.

Just a suggestion

demon1031 wrote:Also, please make sure you try using the 32 bit SSL files first.

If you have the 64-bit Gold version, you must use the 64-bit OpenSSL files. For all other editions (32-bit Gold, Pro, Lite, Trial) you must use the 32-bit OpenSSL files.

Kent Briggs wrote: ↑Mon Mar 30, 2020 8:55 am

demon1031 wrote:Also, please make sure you try using the 32 bit SSL files first.

If you have the 64-bit Gold version, you must use the 64-bit OpenSSL files. For all other editions (32-bit Gold, Pro, Lite, Trial) you must use the 32-bit OpenSSL files.

Hi Kent, I have this same problem (SSL3_Get_RECORD: Wrong Version Number) and I have tried all the proposed solutions. The 64 -bit edition link https://www.briggsoft.com/download/opessl64.zip contains files called 32 bits.
Will it have something to do with? I'm stuck and I have tried with Outlook, Gmail and Yahoo

yilon wrote: ↑Wed Dec 27, 2023 11:00 am Hi Kent, I have this same problem (SSL3_Get_RECORD: Wrong Version Number) and I have tried all the proposed solutions. The 64 -bit edition link https://www.briggsoft.com/download/opessl64.zip contains files called 32 bits.
Will it have something to do with? I'm stuck and I have tried with Outlook, Gmail and Yahoo

The 64-bit files have the same names as the 32-bit files so you can't tell the difference going by that. Look at the file sizes. The 64-bit versions are as follows:

libeay32.dll = 2284544 bytes
ssleay32.dll = 386560 bytes

Note that these should already be in your program folder automatically beginning with version 7.01. The installer will install the right edition for you.