Hey there, I've just updated a system from 13.2-RELEASE to 14.0-RELEASE and have run into a few problems with Jellyfin 10.8.10.

1) It looks like with the upgrade to OpenSSL-3 on 14.0 you need to install the openssl111 port to get Jellyfin running (when installed from packages at least).  Without that installed it's crash on startup like so:
[00:11:31] [INF] [4] Main: Kestrel listening on Any IP4 Address
No usable version of libssl was found
Abort trap


2) After installing the legacy openssl pkg it starts up as expected and the webUI loads.  unfortunately it looks like ffmpeg has issues trying to play back media.  I uninstalled the ffmpeg pkg, and reinstalled - and also verified that I can run ffmpeg in a shell.

This is the error in the logs when i start up jellyfin:

[2023-11-22 00:17:04.193 +00:00] [ERR] [1] MediaBrowser.MediaEncoding.Encoder.MediaEncoder: Error validating encoder
System.ComponentModel.Win32Exception (2): An error occurred trying to start process 'ffmpeg' with working directory '/'. No such file or directory
   at System.Diagnostics.Process.ForkAndExecProcess(ProcessStartInfo startInfo, String resolvedFilename, String[] argv, String[] envp, String cwd, Boolean setCredentials, UInt32 userId, UInt32 groupId, UInt32[] groups, Int32& stdinFd, Int32& stdoutFd, Int32& stderrFd, Boolean usesTerminal, Boolean throwOnNoExec)
   at System.Diagnostics.Process.StartCore(ProcessStartInfo startInfo)
   at System.Diagnostics.Process.Start()
   at MediaBrowser.MediaEncoding.Encoder.EncoderValidator.GetProcessOutput(String path, String arguments, Boolean readStdErr, String testKey)
   at MediaBrowser.MediaEncoding.Encoder.EncoderValidator.ValidateVersion()
[2023-11-22 00:17:04.212 +00:00] [WRN] [1] MediaBrowser.MediaEncoding.Encoder.MediaEncoder: FFmpeg: Failed version check: "ffmpeg"
[2023-11-22 00:17:04.228 +00:00] [INF] [1] MediaBrowser.MediaEncoding.Encoder.MediaEncoder: FFmpeg: ""


Then i get this error when I attempt to playback media:

2023-11-22 00:18:02.232 +00:00] [ERR] [26] Jellyfin.Server.Middleware.ExceptionMiddleware: Error processing request. URL "GET" "/videos/a22bbeb0-697b-7b60-74dc-d5261e29e4e6/hls1/main/0.ts".
System.ArgumentException: FFmpeg path not set.
   at Jellyfin.Api.Helpers.TranscodingJobHelper.StartFfMpeg(StreamState state, String outputPath, String commandLineArguments, HttpRequest request, TranscodingJobType transcodingJobType, CancellationTokenSource cancellationTokenSource, String workingDirectory)
   at Jellyfin.Api.Controllers.DynamicHlsController.GetDynamicSegment(StreamingRequestDto streamingRequest, Int32 segmentId)
   at Jellyfin.Api.Controllers.DynamicHlsController.GetHlsVideoSegment(Guid itemId, String playlistId, Int32 segmentId, String container, Int64 runtimeTicks, Int64 actualSegmentLengthTicks, Nullable`1 static, String params, String tag, String deviceProfileId, String playSessionId, String segmentContainer, Nullable`1 segmentLength, Nullable`1 minSegments, String mediaSourceId, String deviceId, String audioCodec, Nullable`1 enableAutoStreamCopy, Nullable`1 allowVideoStreamCopy, Nullable`1 allowAudioStreamCopy, Nullable`1 breakOnNonKeyFrames, Nullable`1 audioSampleRate, Nullable`1 maxAudioBitDepth, Nullable`1 audioBitRate, Nullable`1 audioChannels, Nullable`1 maxAudioChannels, String profile, String level, Nullable`1 framerate, Nullable`1 maxFramerate, Nullable`1 copyTimestamps, Nullable`1 startTimeTicks, Nullable`1 width, Nullable`1 height, Nullable`1 maxWidth, Nullable`1 maxHeight, Nullable`1 videoBitRate, Nullable`1 subtitleStreamIndex, Nullable`1 subtitleMethod, Nullable`1 maxRefFrames, Nullable`1 maxVideoBitDepth, Nullable`1 requireAvc, Nullable`1 deInterlace, Nullable`1 requireNonAnamorphic, Nullable`1 transcodingMaxAudioChannels, Nullable`1 cpuCoreLimit, String liveStreamId, Nullable`1 enableMpegtsM2TsMode, String videoCodec, String subtitleCodec, String transcodeReasons, Nullable`1 audioStreamIndex, Nullable`1 videoStreamIndex, Nullable`1 context, Dictionary`2 streamOptions)
   at lambda_method1068(Closure , Object )
   at Microsoft.AspNetCore.Mvc.Infrastructure.ActionMethodExecutor.TaskOfActionResultExecutor.Execute(IActionResultTypeMapper mapper, ObjectMethodExecutor executor, Object controller, Object[] arguments)
   at Microsoft.AspNetCore.Mvc.Infrastructure.ControllerActionInvoker.<InvokeActionMethodAsync>g__Awaited|12_0(ControllerActionInvoker invoker, ValueTask`1 actionResultValueTask)
   at Microsoft.AspNetCore.Mvc.Infrastructure.ControllerActionInvoker.<InvokeNextActionFilterAsync>g__Awaited|10_0(ControllerActionInvoker invoker, Task lastTask, State next, Scope scope, Object state, Boolean isCompleted)
   at Microsoft.AspNetCore.Mvc.Infrastructure.ControllerActionInvoker.Rethrow(ActionExecutedContextSealed context)
   at Microsoft.AspNetCore.Mvc.Infrastructure.ControllerActionInvoker.Next(State& next, Scope& scope, Object& state, Boolean& isCompleted)
   at Microsoft.AspNetCore.Mvc.Infrastructure.ControllerActionInvoker.InvokeInnerFilterAsync()
--- End of stack trace from previous location ---
   at Microsoft.AspNetCore.Mvc.Infrastructure.ResourceInvoker.<InvokeNextResourceFilter>g__Awaited|25_0(ResourceInvoker invoker, Task lastTask, State next, Scope scope, Object state, Boolean isCompleted)
   at Microsoft.AspNetCore.Mvc.Infrastructure.ResourceInvoker.Rethrow(ResourceExecutedContextSealed context)
   at Microsoft.AspNetCore.Mvc.Infrastructure.ResourceInvoker.Next(State& next, Scope& scope, Object& state, Boolean& isCompleted)
   at Microsoft.AspNetCore.Mvc.Infrastructure.ResourceInvoker.InvokeFilterPipelineAsync()
--- End of stack trace from previous location ---
   at Microsoft.AspNetCore.Mvc.Infrastructure.ResourceInvoker.<InvokeAsync>g__Awaited|17_0(ResourceInvoker invoker, Task task, IDisposable scope)
   at Microsoft.AspNetCore.Mvc.Infrastructure.ResourceInvoker.<InvokeAsync>g__Awaited|17_0(ResourceInvoker invoker, Task task, IDisposable scope)
   at Microsoft.AspNetCore.Routing.EndpointMiddleware.<Invoke>g__AwaitRequestTask|6_0(Endpoint endpoint, Task requestTask, ILogger logger)
   at Jellyfin.Server.Middleware.ServerStartupMessageMiddleware.Invoke(HttpContext httpContext, IServerApplicationHost serverApplicationHost, ILocalizationManager localizationManager)
   at Jellyfin.Server.Middleware.WebSocketHandlerMiddleware.Invoke(HttpContext httpContext, IWebSocketManager webSocketManager)
   at Jellyfin.Server.Middleware.IpBasedAccessValidationMiddleware.Invoke(HttpContext httpContext, INetworkManager networkManager)
   at Jellyfin.Server.Middleware.LanFilteringMiddleware.Invoke(HttpContext httpContext, INetworkManager networkManager, IServerConfigurationManager serverConfigurationManager)
   at Microsoft.AspNetCore.Authorization.Policy.AuthorizationMiddlewareResultHandler.HandleAsync(RequestDelegate next, HttpContext context, AuthorizationPolicy policy, PolicyAuthorizationResult authorizeResult)
   at Microsoft.AspNetCore.Authorization.AuthorizationMiddleware.Invoke(HttpContext context)
   at Jellyfin.Server.Middleware.QueryStringDecodingMiddleware.Invoke(HttpContext httpContext)
   at Swashbuckle.AspNetCore.ReDoc.ReDocMiddleware.Invoke(HttpContext httpContext)
   at Swashbuckle.AspNetCore.SwaggerUI.SwaggerUIMiddleware.Invoke(HttpContext httpContext)
   at Swashbuckle.AspNetCore.Swagger.SwaggerMiddleware.Invoke(HttpContext httpContext, ISwaggerProvider swaggerProvider)
   at Microsoft.AspNetCore.Authentication.AuthenticationMiddleware.Invoke(HttpContext context)
   at Jellyfin.Server.Middleware.RobotsRedirectionMiddleware.Invoke(HttpContext httpContext)
   at Jellyfin.Server.Middleware.LegacyEmbyRouteRewriteMiddleware.Invoke(HttpContext httpContext)
   at Microsoft.AspNetCore.ResponseCompression.ResponseCompressionMiddleware.InvokeCore(HttpContext context)
   at Jellyfin.Server.Middleware.ResponseTimeMiddleware.Invoke(HttpContext context, IServerConfigurationManager serverConfigurationManager)
   at Jellyfin.Server.Middleware.ExceptionMiddleware.Invoke(HttpContext context)


(interestingly - media i've previously played back works, but new video files throw this error along with an Playback Error in the UI).