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I have recently tried and failed to play a couple of ISO's, which when selected just refuse to play and don't show any notification in the GUI. There are a couple I have, both same series and from same release time - quite old. These both play ok in VLC. Any insights would be appreciated. The behaviour is the same on both my OpenElec and Windows installs.

http://xbmclogs.com/pzy6opmeh - start of playback is about line 1963, for two ISO files. I have tried more recent ISO's I have and they play ok.
Those isos are broken or damaged or dont contain a valid iso structure. Here are the relevant messages you should be looking at.

Code:
18:11:47 T:140081815201536    INFO:   msg: libdvdnav: Using dvdnav version 4.2.1
18:11:47 T:140081815201536   DEBUG: CSMBFile::Open - opened media/Videos/TV/(deleted iso name)/(deleted iso name) S01E05.iso, fd=10000
18:11:47 T:140081815201536    INFO:   msg: libdvdnav:DVDOpenFileUDF:UDFFindFile /VIDEO_TS/VIDEO_TS.IFO failed
18:11:47 T:140081815201536    INFO:   msg: libdvdnav:DVDOpenFileUDF:UDFFindFile /VIDEO_TS/VIDEO_TS.BUP failed
18:11:47 T:140081815201536   DEBUG:   msg: libdvdread: Can't open file VIDEO_TS.IFO.
18:11:47 T:140081815201536   DEBUG:   msg: libdvdnav: vm: failed to read VIDEO_TS.IFO
18:11:47 T:140081815201536   DEBUG: CSMBFile::Close closing fd 10000
18:11:48 T:140081815201536   ERROR: Error on dvdnav_open
18:11:48 T:140081815201536   ERROR: CDVDPlayer::OpenInputStream - error opening [smb://(deleted)/media/Videos/TV/(deleted iso name)/(deleted iso name) S01E05.iso]
18:11:48 T:140081815201536  NOTICE: CDVDPlayer::OnExit()
18:11:48 T:140081815201536   DEBUG: OnPlayBackStopped: play state was 1, starting 1
18:11:48 T:140081815201536   DEBUG: Thread DVDPlayer 140081815201536 terminating
18:11:48 T:140084490704768   DEBUG: OnPlayBackStopped: play state was 3, starting 0
18:11:48 T:140084490704768   DEBUG: CAnnouncementManager - Announcement: OnStop from (deleted)
18:11:48 T:140084490704768   DEBUG: GOT ANNOUNCEMENT, type: 1, from (deleted), message OnStop
18:11:48 T:140084490704768   ERROR: Playlist Player: skipping unplayable item: 0, path [smb://(deleted)/media/Videos/TV/(deleted iso name)/(deleted iso name) S01E05.iso]
Thanks for the pointers, it does seem to be the case that there is something wrong with them. I tried mounting them to re-rip, and that also gives an error to check the media.

Any ideas on how I could fix them? I could try just ripping the main feature, but they have a lot of extras in the iso I'd like to keep, and they are pretty old sources to track down.
No idea at all about that, Google makes some references to IsoBuster, but dont ask me for the process or if it works, my guess is you have slim chances here.
It's worth trying IsoBuster (www.isobuster.com), but do a careful clean of drive and DVD first.
If you cannot mount the media, it may still be possible to grab the data directly, but this can be messy.
Please note that I've used IsoBuster on CDs, but never tested it on DVDs of any sort.
Thanks both for the info. I managed to extract out the VOB files etc from the ISO and they play ok, so I'll have a play around and rebuild them into a new DVD ISO, so looks like sorted.

Should kodi be set to give an error in the GUI this case when it gets an ISO like this that it can't play? At the moment, nothing pops up etc; no 'failed to play' etc.
Open a bug report for the lack of messaging. add debug logs of this issue @ http://trac.kodi.tv

However upgrade your kodi to the final 15 Version before you duplicate the issue and make the report.
Ok uNiversal thanks, have verified still present in 15.0, and raised a Trac log. Thanks.