You may want to read some other active threads here, but based what I have read...

Southwest/Chase have made it clear that the last date for posting to earn the 2019 pass is the December statement. Which then means anything AFTER the December statement will go into 2020. If you look at your actual statement, you will see that printed.

REMINDER: Know your credit card's annual earning cutoff date for Companion Pass. Your December statement closing date will be the last date for purchases made with your Rapid Rewards Credit Card to count towards a Companion Pass for this year. For more details go to Southwest.com/rrterms.

Some folks would say to not spend to go OVER the $5k on the biz card until Jan 1st - but that seems to be a "better safe than sorry" suggestion. Still, I can not find any definitive "rule" that they could process all your charges and actually give the bonus sometime after that close and before January 1st. I really doubt that will happen, but if you were to manage things closely, stay just short of your number until at least Jan 1st.

I will also say there appears to situations where your Jan 3 closing date could be an issue. Apparently, there are some cases where the spend hits on Jan 1st and 2nd (maybe 3rd) and you get those points just fine. BUT, they do not send over the bonus until he following month. Maybe they run the bonus "program" only on certain dates and post it.

So...watch it all closely. And as I recall, the annual fee does not count as spend which you can verify by looking at your first statement and what was sent to WN.

I have both cards and plan to keep the spend below the bonus until the 1st. Luckily for me, both have a mid month close date. I need the CP before Jan 28th trip.