How To Seal Leaking Kitchen Overflow?

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The overflow in my kitchen is leaking (pics attached)

Does anyone know how to seal this?

My overflow is screwed in under the sink

I assume that this leak is due to the rubber washer.
 

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tried this and there was still a trickle of water that would leak

so i removed the sillicone from the overflow and whilst doing this, the washer ripped apart

is there anything else that can be done now?
 
Hmm, sheet of rubber and cut to shape? Others may suggest more silicone without the washer.
 
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after the washer fell apart, I placed lots of silicone (Plumbers Gold) and screwed the part back.

tested after 12hrs

all seemed well initially, then the inevitable trickle of water.

For peace of mind, i am just going to replace the entire sink
 
So am I being OTT by wanting to replace the entire sink?

Is this a repairable job? (by a professional?)

My sink dimensions on top are 860 X 460mm

If I was to replace the sink, in theory would a 860 x 500mm be okay?
 
It is the hole in the worktop that counts which will be roughly 10mm smaller all round, or have a look from under the sink. If you really want to replace the sink then now is a good time.
 

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