This issue has plagued my installation of Orion since 0.99.119 was released. I had tried resetting Orion before via the Debug menu, but this did not fix the issue.
After rm
-ing the ~/Library/Application Support/Orion
to remove all extensions data, I went ahead and tested all the extensions I use on Firefox (minus Tree Style Tabs).
Dark Reader
by itself, works 95% of the time. It's not exact, but I would say every 7th reboot of Orion results in Dark Reader never loading in properly, just like in @lazylizard42's screenshot. This can be fixed by disabling and re-enabling Dark Reader in Extensions Manager.
Enhancer for YouTube
does not affect Dark Reader.
However, the following extensions either lower this success rate or completely kill Dark Reader, every restart:
- Rikaichamp
- BetterTTV
- Bitwarden
- Multiselect for YouTube
- Return YouTube Dislike
- SponsorBlock for YouTube
For the time being, I've taken refuge on Firefox with firefox-safari-style and Tree Style Tabs to emulate Orion's beautiful design:

Vs. Orion and its natural beauty:

Orion 0.99.119-beta (WebKit 615.1.1)
macOS Version 13.0 (Build 22A5331f)
MacBookAir10,1
Session Info:
- Open windows => 1
- Pinned tabs => 0
- Active window tabs => 1
- Active tab url => orion://newtab/
Enabled Extensions:
- Dark Reader (firefox)
- Enhancer for YouTubeā¢ (firefox)
Disabled Extensions:
Non Default Settings:
- ContentBlockerLastUpdated => 2022-08-12 00:00:00 +0000
- ShowFavoritesOnStartPage => 0
- ShowTopSitesOnStartPage => 0
- ShowReadingListOnStartPage => 0
- ShowRecommendationsOnStartPage => 0
- ShowBackgroundImageOnStartPage => 0
- isBackgroundImageDarkOnStartPage => 1
- overflowMenuItems => (
)
- WebAutomaticSpellingCorrectionEnabled => 0
- WebContinuousSpellCheckingEnabled => 0
- WebAutomaticQuoteSubstitutionEnabled => 0
- WebAutomaticDashSubstitutionEnabled => 0
- ShouldShowWelcomeAnimation => 0
- FirstLaunch => 0
- FirstTimeWebExtensionNotice => 1
- HomePageURL =>
- HyperlinkAuditingEnabled => 0
- LastUsedBuildVersion => 119
- PreCompiledContentRuleListVersion => 119
- LastCrashCheckDate => 2022-09-07 01:43:07 +0000
- NetworkPredictionEnabled => 0
- NextDownloadID => 26
- SavedWindowSize => 1462.0,964.0
- SavedWindowPosition => 109.0,31.0
- TabStyle => treeStyle
- BookmarksSidebarVisible => 1
- BookmarksSidebarWidth => 279.5
- QuitWithConfirmation => 0
- ActiveLibraryTab => extensions
- SyncEnabled => 1
- BookmarksLastSynced => 1662514987615.837
- ReadingListLastSynced => 1662514987616.419