Hi Jeff ( @Placebophile),
I edited the name on the 1st two sides of the BBF album I ripped to be like this:
Unfortunately, this did not cause Side 2 to play after side 1.
So I clicked the “Shuffle toggle” icon and tried again - same result. 
I will now re-create the FLAC files from the Audacity rips of these 2 sides … and see if I can add some numbers during the tagging procss which Audacity asks me to do.
A completely random track or a random track from the same album?
Seems we’ve eliminated shuffle as a variable.
Could you confirm:
We posted at the same time.
Reading your update now……
I’m a bit baffled but suspect the files need track numbers either in metadata tags or via Roon Edits.
I can really only guess as my library files have always been tagged in an editor prior to importing into Roon.
Following the 3 points in my recent previous post would check off some more variables.
This next point is pure speculation but I’m wondering if the Roon database isn’t updating properly to changes to your files?
It might not hurt to shut Roon down and delete the old files from Roon’s storage folder (make sure you have copies elsewhere).
Then restart Roon so it does a database refresh.
Once that’s done you can go to Settings>Library>Clean Up Library
and delete the old entries.
Then add the new files.
Hi Jeff,
I will check back to your previous post soon - but I found the “Settings” (gear wheel) icon and clicked on “Track #” … so that it now appears.
See here:
The tracks shown are a combination of LP sides that I have ripped … and some HD tracks that a mate of mine gave me, on a USB stick.
Note the two “Lessons for the Lyra Violl” tracks; the fact that Side 1 has ‘1’ in the track no. - whilst Side 2 has ‘2’ in the track no. - does not cause Side 2 to play, immediately after Side 1. 
Also, I note that there several track #2s in the Snip I posted … so I’m unsure as to what purpose the ‘Track #’ has?
That’s a fantastic collection of diverse tracks!
I appreciate all those artists.
I’m not sure what your screencap is of.
I run Roon Server and control it from mobile devices so things look a little different for me.
But this has me thinking about the Roon queue and what method you’re using to add tracks to the queue/start them playing.
Are you maybe playing albums from the My Library>Tracks page rather than the page for a particular album?
This might explain things.
Viewing the queue after starting play might give some clues.
Sorry this has become so sprawling and ridden with variables.
Not having hands on access to your setup combined with Roon’s many variables makes things rather abstract.
But I think the key thing here is to get your files properly tagged with Artist, Album, Track Number, Title.
Normally Roon can do a reasonably good job of figuring that stuff out without detailed tagging but as your rips are from LPs and the number of tracks and track lengths differ from a typical CD rip it can’t.
Thanks for your continuing help, Jeff. 
I run Roon on a dedicated PC; the only other apps on it are Microsoft Edge (where this conversation displays) and Audacity (for the LP ripping).
Control of Roon is via the keyboard and screen attached to the PC.
I play tracks by selecting ‘My Library / Tracks’ from the menu on the LHS of the Roon screen - which lists all the tracks I have imported into Roon … and then clicking on the one I want to play, first up.
I don’t know how else to play the tracks!
Instead of starting from Tracks: What happens if you go to Albums and select an album?
Are the tracks listed in the correct order and if you press “Play Now” from that page do the tracks play in order?
You could also just go to the queue page after starting play as that will show what tracks are being played and in what order.
Thanks, Jeff.
I chose ‘Albums’ - and saw this screen:
This did play all 4 sides in order - and then Roon went off to play another track in another part of the “Track List”!
So we’ve moved forwards a step or two - yay!
Are you able to tell me what the numbers in the last column before the “…” signify?
Thanks again.
Interestingly enough, when I select ‘Albums’ and see this:
… the 4 sides do play in order, one after another.
But if I select side 1 when in the ‘Tracks’ list - see here:
… it went through sides 1, 2 & 3 in order - but instead of then playing side 4 … it jumped to another track!
But at least I can play all 4 sides in order, when I’m using the ‘Albums’ list!
Check your queue and see if Roon Radio is enabled.
I think it’s enabled by default.
This would explain why it’s playing other tracks after an album is finished.
The indicator you asked about is your play counts for that track.
I never play from the tracks page so I can’t really explain that behaviour other than to guess it might have something to do with how the tracks page is ordered - you can change it by clicking the parameter names near the top - so it might appear to be organized one way but it’s not.
Like, it may seem to be ordered by track number but it’s actually ordered by track title as numbers appear in your titles.
…I’m struggling to clearly explain what I mean by this.
If you view your queue immediately after starting play it might give some insight
Aah, OK Jeff.
I’m afraid I have no idea how to reach the screen you showed. 
Forgot you’re using the desktop version.
Click the highlighted button in my pic to get to the queue.
You’ll see Roon Radio info near the bottom.
As mentioned, getting to know how the queue works will likely help you understand playback in Roon.
Thank you, Jeff.
I clicked on that button and have now turned off ‘Roon Radio’.
I will see whether that changes the playback behaviour, tomorrow - and report back.
From your screenshot of the Mr Machine album page, it is clear that your file metadata is in a poor state.
I think you need to use a metadata editor to get your metadata in order. Then this album would look like this:
Edit: I see now that you’re ripping LPs a side at a time. Then it’s going to be difficult to get a match with releases in the Roon database. You need to use a metadata editor to assign track (side?) numbers to your files to build up the correct playing sequence, and to add Album art metadata.
(Deleted, others already explained this)
In general, if I went through the huge hassle of ripping my vinyl, I would do it once and do it properly by splitting up the sides into tracks.
Secondly, it’s going to be a big hassle in the best case to make Roon identify even good rips (with individual tracks) and associate them properly with its cloud metadata for every album - unless you take care to have track lengths consistent with digital releases. If it can’t find the proper associations, many of Roon’s best features aren’t going to work as intended (automatic credits, albums reviews), and so I am not sure if Roon is the best tool for this in the first place.
Thank you, @Suedkiez.
Yes, I appreciate I won’t be able to take advantage of many good Roon features - but splitting a side into tracks … is a ‘bridge too far’, AFAIAC!
My reason for wanting to use Roon to play my vinyl - rather than playing it directly, outside of Roon - is so that I can take advantage of Roon’s convolution capabilities.
A mate has done this (although he gets his music from QoBuz, not rips) and Roon convolution produced a significant SQ improvement for his MBL 101s. The same thing happened when he added convolution to another mate’s streaming system (with B&W standmounts).
And @Geoff_Coupe, yes, my metadata is pathetic! 
Someone earlier suggested a metadata editor to use … I’m thinking I will:
1. go through the process of ripping - since, using the knowledge I’ve gained so far with all your responses, I can at least make sure the sides play in sequential order, then
2. use a metadata editor to “smarten up” the music tracks.
