Anonymous monetary gift

Are you talking via online banking, or another way?

I’ve done it a couple of times but not anonymously.
Both times I just put the cash in their had, gave them my Meryl look which they know means there is no argument about this.
Both times I gave the money, said a few words and walked away.

Put it in an envelope and stick it through her door?

I have a scheme to do this when I win millions on the lottery and don’t want to let anyone know but want to share it. It’s a bit complicated though. A bit too OTT for your needs.
If you put it through her letter box anonymously she may be a bit worried and reluctant to spend it, just in case it was the wrong letterbox and someone may turn up to claim it, so if you decide on that option do make sure she knows it’s for her.

I think that receipt (in any way), of anonymous money could be very worrying. Would be likely to cause more stress than happiness, and probably just be put aside in case it was claimed back.

Just talk to your friend and explain that you really would be so happy if they would accept a gift from you - in fact it would cause more joy to the giver than the recipient.

If your friend is fiercely independent and proud, an anonymous gift of money may be the worst thing you could do. She may wonder how many people know she's struggling.
I would give her a gift and tell her it comes with love. If she protests, ask her to pay it forward if she gets in a position to do that. I've been a recipient of a monetary gift from my dearest friend before she died. It helped me out immensely and was gratefully received.

I agree Franbern. Receiving money with no idea where it came from would be very worrying and it would probably not be spent for fear of it having been given mistakenly.

We once took cash to seriously struggling friends living some distance away. It was not long before Christmas, so I put it in a Christmas card, and gave it to her while her dh was out of the way - I thought he might refuse it out of pride.
If we’d offered it e.g. over the phone, I know they’d have refused.
As it was, there was no argument at all.
As I said to her, I know you’d do the same for us, which was true.

As others have said, don't give it anonymously, your friend might fret and be scared to spend it.

Like Meryl I've done it directly with few words and a look.

I am thoroughly appalled by recent treatment from John Lewis but have vouchers still to come. Could you pretend something similar with an envelope of gift vouchers and ask your friend if they would do you a favour by spending them on herself . Or is that too devious?

the arrival of anonymous money, by any route, could give rise to fears about money laundering, bribery, corruption, or other criminality.
she might go to the police.
i think i would.

I think money in an envelope, through the letterbox would be best. Maybe put her name on the envelope with a message such as ‘ for a special person ‘. Typed and stuck on to keep it anonymous.

If it’s a considerable amount, you could use a solicitor to be the go between. They’d be bound by confidentiality.

if that happened to me, i would then be anxiously awaiting the next envelope through the door which reminded me that i was now indebted to them and instructions would follow shortly of what i was expected to do for them.
and of course, they know where i live . . .

This can be so difficult, and a bit of a minefield.
4/5 years ago, a friend was struggling. Her daughter needed medical treatment and no way could she afford a private consultation. I offered to pay, as a gift and put the money in an envelope and gave it to her, with a letter, no strings attached. She came round a few days later and returned it in full, saying that she couldn't accept it.
I still wished that she had, but had to accept her decision.

I would be honest about it, saying that you can afford and want to give her some money to help out and never want to speak about it again, then transfer some money.

It depends how much it is but you could say you’ve won the Premium Bonds and are giving all your friends a sum of money to spend however they want.

Make it sound like to say no when everybody else has said oh lovely thank you, would make her an odd one out.