Preferred connection time between Long Distance (LD) trains

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I know there are people who regularly plan to spend the night in Chicago rather than relying on Amtrak's same-day connections, but in 20-plus cross-country trips we have never done this.
We’ve done 11 trips east on SWC No. 4 where we had a same day connection in Chicago with CL No. 30. We’ve made all of them with the exception of one and that was due to extreme weather encountered in Missouri which delayed our train by 7 hours. Fortunately, we had a guaranteed connection and Amtrak put us up in a hotel for the night, gave each of us $40 worth of food coupons, and sent us out on the next day’s CL No. 30 which, incidentally, arrived at our destination (Toledo) only three minutes late. We’ll be doing this trip again next month and we fully expect to make our same day connection in Chicago.
 
Are guaranteed connections only between LD trains?
For instance the LSL is schecduled to arrive at BOS by 2032. The last Downeaster to Portland is scheduled to leave BON at 2325. Is this a guaranteed connection?
Guaranteed connections exist between any types of trains, LD such as the LSL and corridor such as the Downeaster. The general guideline is 60 minutes between trains except LD to NEC, which is 120 minutes. There are many exceptions to these guidelines and individual connections themselves are set in ARROW on a case by case basis. You cannot just assume a connection is guaranteed by looking at the connection time.

Actual guaranteed connections are shown on Amtrak.com by entering your origin and destination under the "one way" or "round trip" option. Any connections it returns are guaranteed by definition. There are some exceptions to this, having to do with the kludgy way connections have to be set up in ARROW, but that's the general rule.

The "Schedules" tab should show the same thing.

So enter your origin and destination and see what comes back. If it returns a self transfer between BOS and BON and the 2325 Downeaster, it is guaranteed. If it isn't and a "no trains available" response is returned, it is probably not. I say probably because of the kludge I mentioned before. In that case, there are ways to confirm it is indeed not guaranteed.
 
If it returns a self transfer between BOS and BON and the 2325 Downeaster, it is guaranteed. If it isn't and a "no trains available" response is returned, it is probably not. I
This got me recalling when Amtrak still operated from New York’s Grand Central Terminal. Back then, they provided a dedicated “Thruway” bus to transfer passengers to or from Penn Station, with connecting trains.
Wondering why they don’t do similar at Boston between North Station and either South Station or Back Bay, whichever is easier?🤔
 
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