By way of update, I've just gone ahead and replaced the seal. So far, so good.
Nuova Simonelli Personal 1 ¦ Mazzer SJ
NS seals are pretty confusing, even for their distributors. They have flat and conical in 2 different thicknesses. Either shape works but from my dealings it seems that it is up to preference of the local distributor or the end user or whether they favour flat or conicals.
On the conicals the flat side faces up, the angled side faces down. A little lubricant on a seal does help the initial insertion. A sheen of lubricant is all you need, not big globs of the stuff. On the seals I make the 8.3mm are red and the 9mm are blue.
I've had this exact same problem with my Gaggia Classic recently. Basically nothing changed but it seemed to start happening and new seals (either silicon or OEM) didn't solve it.
Rocket Appartamento | Mahlkonig Vario | 58mm Rocket tamper | AeroPress | VST 18g basket | HappyDonkey Bottomless PortaFilter
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