Ok, this makes no sense to me but... I did exactly as you asked, turned on connection doctor and then sent tried to send an email from one email address to another... Results below...
INITIATING CONNECTION Aug 22 17:57:47.334 host:relay.plus.net -- port:25 -- socket:0x0 -- thread:0x600000871100
CONNECTED Aug 22 17:57:47.359 [kCFStreamSocketSecurityLevelNone] -- host:relay.plus.net -- port:25 -- socket:0x6000004c8030 -- thread:0x600000871100
READ Aug 22 17:57:48.514 [kCFStreamSocketSecurityLevelNone] -- host:relay.plus.net -- port:25 -- socket:0x6000004c8030 -- thread:0x600000871100
220 avasout05 smtp relay.plus.net
WROTE Aug 22 17:57:48.524 [kCFStreamSocketSecurityLevelNone] -- host:relay.plus.net -- port:25 -- socket:0x6000004c8030 -- thread:0x600000871100
EHLO unknown-20:c9:d0:e4:8b:1f.home
READ Aug 22 17:57:48.542 [kCFStreamSocketSecurityLevelNone] -- host:relay.plus.net -- port:25 -- socket:0x6000004c8030 -- thread:0x600000871100
501 EHLO requires valid address
WROTE Aug 22 17:57:48.543 [kCFStreamSocketSecurityLevelNone] -- host:relay.plus.net -- port:25 -- socket:0x6000004c8030 -- thread:0x600000871100
EHLO unknown-20:c9:d0:e4:8b:1f.home
READ Aug 22 17:57:48.563 [kCFStreamSocketSecurityLevelNone] -- host:relay.plus.net -- port:25 -- socket:0x6000004c8030 -- thread:0x600000871100
501 EHLO requires valid address
WROTE Aug 22 17:57:48.563 [kCFStreamSocketSecurityLevelNone] -- host:relay.plus.net -- port:25 -- socket:0x6000004c8030 -- thread:0x600000871100
RSET
READ Aug 22 17:57:48.584 [kCFStreamSocketSecurityLevelNone] -- host:relay.plus.net -- port:25 -- socket:0x6000004c8030 -- thread:0x600000871100
250 OK
WROTE Aug 22 17:57:48.584 [kCFStreamSocketSecurityLevelNone] -- host:relay.plus.net -- port:25 -- socket:0x6000004c8030 -- thread:0x600000871100
HELO unknown-20:c9:d0:e4:8b:1f.home
READ Aug 22 17:57:48.603 [kCFStreamSocketSecurityLevelNone] -- host:relay.plus.net -- port:25 -- socket:0x6000004c8030 -- thread:0x600000871100
501 HELO requires valid address
INITIATING CONNECTION Aug 22 17:57:48.604 host:relay.plus.net -- port:25 -- socket:0x0 -- thread:0x600000871100
CONNECTED Aug 22 17:57:48.628 [kCFStreamSocketSecurityLevelNone] -- host:relay.plus.net -- port:25 -- socket:0x6000004ce310 -- thread:0x600000871100
READ Aug 22 17:57:50.050 [kCFStreamSocketSecurityLevelNone] -- host:relay.plus.net -- port:25 -- socket:0x6000004ce310 -- thread:0x600000871100
220 avasout05 smtp relay.plus.net
WROTE Aug 22 17:57:50.050 [kCFStreamSocketSecurityLevelNone] -- host:relay.plus.net -- port:25 -- socket:0x6000004ce310 -- thread:0x600000871100
HELO unknown-20:c9:d0:e4:8b:1f.home
READ Aug 22 17:57:50.073 [kCFStreamSocketSecurityLevelNone] -- host:relay.plus.net -- port:25 -- socket:0x6000004ce310 -- thread:0x600000871100
501 HELO requires valid address
WROTE Aug 22 17:57:50.074 [kCFStreamSocketSecurityLevelNone] -- host:relay.plus.net -- port:25 -- socket:0x6000004ce310 -- thread:0x600000871100
HELO unknown-20:c9:d0:e4:8b:1f.home
READ Aug 22 17:57:50.094 [kCFStreamSocketSecurityLevelNone] -- host:relay.plus.net -- port:25 -- socket:0x6000004ce310 -- thread:0x600000871100
501 HELO requires valid address