am I being too cautious?

[MrsDeathOfRats]

Woman has won a bag I've sold. Another bag I'm selling ends in 3 days and she asked me not to post bag 1 incase she wins bag 2 also. Fine. No problem.

She has paid for bag 1. And asked if she wins can I refund her some postage and send them together.
I said I will refund her whole payment and send her a combined invoice but she seems irritated. DP thinks I'm being too careful.

Am I correct in thinking two separate sales with one tracking number leaves me open to having her claim that I only posted one item? Which could result in Ebay refunding her for one of them?

You sound a bit paranoid, but having only one parcel also protects her a little. Because there's only one thing that can go wrong in the delivery service. I would pitch it to her that way.

She won't pay any more or have to click any extra buttons, just wait for 2nd invoice if she wins 2nd bag. Else her first payment is fine & can proceed without her doing anything more.

I've been ripped off so many times on eBay. And messed around so much.

I learnt the hard way about the PayPal/collecting issue and had to refund someone a considerable amount because of my naivety. So I am just making sure I'm not putting myself in a dodgy position again.

I realise if she doesn't win bag2 then she has already paid and therefore has nothing to do.
I just didn't see why she should be annoyed at me wanting to protect myself

yes I would refund and ask her to pay for both together - I agree with you.

I'm paranoid too - due to previous bad experience where eBay awarded in favour of buyer who was trying to scam me by saying I'd only sent one item when I'd combined to save them postage

This week sold 4 items to same person - all reasonably high value - they are not happy with me as I sent them in 4 separate tracked parcels to protect myself

I did not offer reduced postage in listing, and if they had been won by 4 different people would have been same for me cost wise - I always price postage as near as possible to actual often losing out myself by time you take off fees etc