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At this point you'd be relying on the goodwill of Eurostar. The NightJet might well run too late to make the earlier connection, and there is no formal connection protection on Eurostar as a result of this delay.
OP's option 2 is far more resilient. Nearly two hours is a lot of time to make...
It is *possible* that they have made a mistaken assumption at some point, and are treating this as if you held no railcard at the time of the journey in question, and therefore looking at it as if you’ve only acquired a railcard when challenged.
As to how best to handle that with them now, I...
For a digital railcard, they’d have the details of the transaction used to buy it.
The relevance is: their behaviour/approach is more what you might expect if the railcard produced *wasn’t* valid at the time of the journey.
Sorry, this is an important point and the previous question (and therefore answer) are unclear.
Did you purchase the railcard before, or after, the time at which you were asked to show the railcard?
You're correct about that restriction and I will amend my post. I notice that there is a specific 'unpublished restriction' for arriving at STP before 1004. Someone more knowledgeable than me will have to intervene to tell us if the TOC can use an unpublished restriction intended for a journey...
https://www.nationalrail.co.uk/travel-information/travelling-in-london/ suggests you should be fine:
Think the time restriction is still an issue - more in a newer post be
However, your ticket was not valid to arrive at St Pancras on any TOC before 1002. Restriction 4A is linked to from your...
It's annoying that the booking sites don't recognise it though - this prevented me being certain enough to use the route for a longer journey a few weeks back.
The age of the system, the age of the ticketing standard and the original specification/purpose of the system would all be relevant considerations here.
Spotted in this morning's disruption (mis)information relating to a train fault breaking Thameslink for the morning commute, some good news for fans of unexpected diversions via Barbican. Reminded me of this abandoned stations page.
Edit: hyperlink and quoted text added at moderator request...
Personally, thinking about trying to keep this journey as practical as possible, I'd suggest changing at Farringdon for Thameslink two stops south to Blackfriars. There is a direct lift from the Elizabeth Line platform level to the southbound Thameslink platform and you can take any train from...