I want to help.

Well, I'm going to disagree with just about everybody else. I would say yes, go ahead and help, but the way you do it is key.

In your shoes I would tell the woman you're working with that someone who wants to remain anonymous has suggested that she would like to help out a client by paying a bill and that you would like to nominate this lady. Then you can make arrangements to pay the bill without handing over any cash at all. I do this frequently in a number of situations and all you need are the recipient company's bank details and a name, address and reference number for the account being paid.

Doing it this way means that you are not setting a precedent for handing over cash, you know the bill will be paid and you can sleep easy knowing that you have alleviated at least the current crisis.

In my role I am in a position to make conditions when I'm administering money and I would strongly suggest to the client that she engages with CAP (Christians Against Poverty) or Stepchange in order to ensure that her financial difficulties are addressed.

No. Absolutely not, for all the reasons given by other posters.
I think this lady has sussed you out as a soft touch/sympathetic to her plight but you would be walking a dangerous path.
The charity perhaps knows her better than you do and, as she has been receiving help over the long term, it possibly shows that she is not willing to help herself.
They are not there to give long term support but to help over the crisis, whatever that may be.
Don't get personally involved.

My granny used to help people anonymously by sending gifts through the post or leaving cash in a kitchen drawer after visiting. She sent a coat and a ton of coal that I know of and probably other things too. Maybe a good way to go then nobody will know it's you

I totally agree with all the other posters - no, don't give money for all the reasons listed above. Bless you for your kind heart, though.

No. It might make you feel better, but there is no guarantee that the 'dysfunctional' family would not appropriate the money and use it in ways you would not wish. I would not get involved on a personal level and it sounds rather that the charity may know more than you do about her circumstances. I suspect your offering - very generous and heartfelt though it is - might be the start of a slippery slope that could end in you losing your position, or worse. Please don't do it.

I am afraid I agree with the others, handing over what would be a large cash sum to her is not a good idea. I am sorry but I don't think you should get too involved. Could you have another go at getting her the help she clearly needs. Are they refusing help because she keeps running up debts however much help she has had? What would you feel if you handed over the money and she came to you for more?

Absolutely no! You could open a big can of worms.....by all means support and help her but giving her cash is a terrible idea. As someone else said....buy her some groceries....take her out for a meal....but not cash and certainly not large sums....would you be prepared or able to continue hand outs if she came back for more??

I have to agree with everyone else. I don't think it would be a one off - but possibly she would come back again and again and would you be able to say no? As has been said charities aim to help people achieve independence, if you give her money you would be undoing that work. Why do you feel the charity is treating her badly? Are there other charities you could point her towards who you think may be more sympathetic towards her?

How kind you are. Could you perhaps give her , as gillybob suggested, something that might help out with an immediate need, like enough food for a complete meal so that at least she has eaten properly on that day? Handing over cash is probably not the best idea as she could lose it, and/or the dysfunctional family could decide on a use for it far removed from your good intentions.

I agree , no,, it is very hard, I can understand how you feel, in the past I have had situations like this.. it hurts, but no.

is there no way you can go to someone at the charity and get them sorted? I so hate it when people abuse power like this.. Charity Commissioners if they are not behaving properly?

No, no and no.
By helping her you will cross many boundaries that are there to protect you.
The golden rule is never to get involved.
Has this woman manipulated you because you’re a soft touch?
What if after an initial payment she started to ask for more? What if she found out where you lived? Is she involved with criminal activity/drugs?
I am sure your intentions are good but the consequences could be dreadful.
Please do not get involved any further.

I am afraid I also agree with everybody- as BlueBelle stated, you will end up having your good nature abused. That is far too much money to hand over and it would never end- she and her family would know where to go if they had more problems.

My first thought was maybe extra groceries but again, I think not. You should not get so personally involved and this woman has recognised that.

Oh gosh no, please don't get personally involved. There are very good reasons why charities and welfare organisations keep a formal 'distance' between the volunteers/workers and their customers. Do you honestly believe that giving her a cash gift would be the end of it? That she'd pay her outstanding bills and thereafter be solvent and need no further help? No, of course not. And she would come to you again and again.

What these organisations are hoping to do is to help people take control of their lives and responsibilities. Giving her money is doing the exact opposite. And on a more personal note for you, if the charity found out you'd done this, you would be 'let go' from your voluntary post.

Please don't do it.

I don’t think this would be a good idea at all and totally agree with Sodapop there is a reason there are limits You might think you are a good judge of character but absolutely no one can be sure of another I thought I was, but have had my good nature abused
This would not be the right way to go I m afraid

I agree with Kitty and gillybob it would not be a good idea to give cash to the lady. I would also advise against getting personally involved with people using your charity organization.
This may seem harsh but there are rules around this for very good reasons. I'm sure your charity has these guidelines in place. You obviously have a kind heart and want to help but this is not the way.

Without going into the ins and outs as to how this poor lady is in the position she is Dawn22 ..... would it be possible for you to help her in other ways rather than handing her £200 that at worst night not be spent In the way you would hope ( you did say she has a dysfunctional family) . Perhaps buy her some much needed groceries , clothing, or pay an overdue bill for her but I really wouldn’t hand over cash .

You are clearly a very kind person Dawn22 and this lady is lucky to know you .

I think that would be a bad idea and would counsel against it.