Pasting text is definitley funky. Sometimes it pastes it twice. But In this case it really struggled
Full log here
2023-02-27 23:36:55.071141+0000 TextAloud[59198:5781890] [claims] Upload preparation for claim 78F96489-3930-452F-9538-0C726F0A6FBC completed with error: Error Domain=NSCocoaErrorDomain Code=260 "The file “dbdc3267e451b4caf6b59972daad48652ceca071” couldn’t be opened because there is no such file." UserInfo={NSURL=file:///Users/willwade-personal/Library/Developer/CoreSimulator/Devices/B4E7C980-0619-4FC9-BEA0-CB94CEAE849B/data/Library/Caches/com.apple.Pasteboard/eb77e5f8f043896faf63b5041f0fbd121db984dd/dbdc3267e451b4caf6b59972daad48652ceca071, NSFilePath=/Users/willwade-personal/Library/Developer/CoreSimulator/Devices/B4E7C980-0619-4FC9-BEA0-CB94CEAE849B/data/Library/Caches/com.apple.Pasteboard/eb77e5f8f043896faf63b5041f0fbd121db984dd/dbdc3267e451b4caf6b59972daad48652ceca071, NSUnderlyingError=0x600001c51770 {Error Domain=NSPOSIXErrorDomain Code=2 "No such file or directory"}} 2023-02-27 23:36:55.071696+0000 TextAloud[59198:5781890] [claims] Claim 78F96489-3930-452F-9538-0C726F0A6FBC failed during preparing for uploading due to error: Error Domain=NSCocoaErrorDomain Code=260 "The file “dbdc3267e451b4caf6b59972daad48652ceca071” couldn’t be opened because there is no such file." UserInfo={NSURL=file:///Users/willwade-personal/Library/Developer/CoreSimulator/Devices/B4E7C980-0619-4FC9-BEA0-CB94CEAE849B/data/Library/Caches/com.apple.Pasteboard/eb77e5f8f043896faf63b5041f0fbd121db984dd/dbdc3267e451b4caf6b59972daad48652ceca071, NSFilePath=/Users/willwade-personal/Library/Developer/CoreSimulator/Devices/B4E7C980-0619-4FC9-BEA0-CB94CEAE849B/data/Library/Caches/com.apple.Pasteboard/eb77e5f8f043896faf63b5041f0fbd121db984dd/dbdc3267e451b4caf6b59972daad48652ceca071, NSUnderlyingError=0x600001c51770 {Error Domain=NSPOSIXErrorDomain Code=2 "No such file or directory"}} 2023-02-27 23:36:55.420745+0000 TextAloud[59198:5781756] [claims] Upload preparation for claim CADB236A-EBB4-494D-A393-BA9B2ED81FF1 completed with error: Error Domain=NSCocoaErrorDomain Code=260 "The file “dbdc3267e451b4caf6b59972daad48652ceca071” couldn’t be opened because there is no such file." UserInfo={NSURL=file:///Users/willwade-personal/Library/Developer/CoreSimulator/Devices/B4E7C980-0619-4FC9-BEA0-CB94CEAE849B/data/Library/Caches/com.apple.Pasteboard/eb77e5f8f043896faf63b5041f0fbd121db984dd/dbdc3267e451b4caf6b59972daad48652ceca071, NSFilePath=/Users/willwade-personal/Library/Developer/CoreSimulator/Devices/B4E7C980-0619-4FC9-BEA0-CB94CEAE849B/data/Library/Caches/com.apple.Pasteboard/eb77e5f8f043896faf63b5041f0fbd121db984dd/dbdc3267e451b4caf6b59972daad48652ceca071, NSUnderlyingError=0x600001c40840 {Error Domain=NSPOSIXErrorDomain Code=2 "No such file or directory"}} 2023-02-27 23:36:55.421287+0000 TextAloud[59198:5781756] [claims] Claim CADB236A-EBB4-494D-A393-BA9B2ED81FF1 failed during preparing for uploading due to error: Error Domain=NSCocoaErrorDomain Code=260 "The file “dbdc3267e451b4caf6b59972daad48652ceca071” couldn’t be opened because there is no such file." UserInfo={NSURL=file:///Users/willwade-personal/Library/Developer/CoreSimulator/Devices/B4E7C980-0619-4FC9-BEA0-CB94CEAE849B/data/Library/Caches/com.apple.Pasteboard/eb77e5f8f043896faf63b5041f0fbd121db984dd/dbdc3267e451b4caf6b59972daad48652ceca071, NSFilePath=/Users/willwade-personal/Library/Developer/CoreSimulator/Devices/B4E7C980-0619-4FC9-BEA0-CB94CEAE849B/data/Library/Caches/com.apple.Pasteboard/eb77e5f8f043896faf63b5041f0fbd121db984dd/dbdc3267e451b4caf6b59972daad48652ceca071, NSUnderlyingError=0x600001c40840 {Error Domain=NSPOSIXErrorDomain Code=2 "No such file or directory"}} 2023-02-27 23:36:55.522460+0000 TextAloud[59198:5781890] [claims] Upload preparation for claim A6500EC6-2A8A-4091-ADCD-4338260FEDA9 completed with error: Error Domain=NSCocoaErrorDomain Code=260 "The file “dbdc3267e451b4caf6b59972daad48652ceca071” couldn’t be opened because there is no such file." UserInfo={NSURL=file:///Users/willwade-personal/Library/Developer/CoreSimulator/Devices/B4E7C980-0619-4FC9-BEA0-CB94CEAE849B/data/Library/Caches/com.apple.Pasteboard/eb77e5f8f043896faf63b5041f0fbd121db984dd/dbdc3267e451b4caf6b59972daad48652ceca071, NSFilePath=/Users/willwade-personal/Library/Developer/CoreSimulator/Devices/B4E7C980-0619-4FC9-BEA0-CB94CEAE849B/data/Library/Caches/com.apple.Pasteboard/eb77e5f8f043896faf63b5041f0fbd121db984dd/dbdc3267e451b4caf6b59972daad48652ceca071, NSUnderlyingError=0x600001c509f0 {Error Domain=NSPOSIXErrorDomain Code=2 "No such file or directory"}} 2023-02-27 23:36:55.523043+0000 TextAloud[59198:5781890] [claims] Claim A6500EC6-2A8A-4091-ADCD-4338260FEDA9 failed during preparing for uploading due to error: Error Domain=NSCocoaErrorDomain Code=260 "The file “dbdc3267e451b4caf6b59972daad48652ceca071” couldn’t be opened because there is no such file." UserInfo={NSURL=file:///Users/willwade-personal/Library/Developer/CoreSimulator/Devices/B4E7C980-0619-4FC9-BEA0-CB94CEAE849B/data/Library/Caches/com.apple.Pasteboard/eb77e5f8f043896faf63b5041f0fbd121db984dd/dbdc3267e451b4caf6b59972daad48652ceca071, NSFilePath=/Users/willwade-personal/Library/Developer/CoreSimulator/Devices/B4E7C980-0619-4FC9-BEA0-CB94CEAE849B/data/Library/Caches/com.apple.Pasteboard/eb77e5f8f043896faf63b5041f0fbd121db984dd/dbdc3267e451b4caf6b59972daad48652ceca071, NSUnderlyingError=0x600001c509f0 {Error Domain=NSPOSIXErrorDomain Code=2 "No such file or directory"}} 2023-02-27 23:36:55.624429+0000 TextAloud[59198:5782367] [claims] Upload preparation for claim BB0A3B69-1526-4470-B2A8-69237A161EF1 completed with error: Error Domain=NSCocoaErrorDomain Code=260 "The file “dbdc3267e451b4caf6b59972daad48652ceca071” couldn’t be opened because there is no such file." UserInfo={NSURL=file:///Users/willwade-personal/Library/Developer/CoreSimulator/Devices/B4E7C980-0619-4FC9-BEA0-CB94CEAE849B/data/Library/Caches/com.apple.Pasteboard/eb77e5f8f043896faf63b5041f0fbd121db984dd/dbdc3267e451b4caf6b59972daad48652ceca071, NSFilePath=/Users/willwade-personal/Library/Developer/CoreSimulator/Devices/B4E7C980-0619-4FC9-BEA0-CB94CEAE849B/data/Library/Caches/com.apple.Pasteboard/eb77e5f8f043896faf63b5041f0fbd121db984dd/dbdc3267e451b4caf6b59972daad48652ceca071, NSUnderlyingError=0x600001c0a250 {Error Domain=NSPOSIXErrorDomain Code=2 "No such file or directory"}} 2023-02-27 23:36:55.624959+0000 TextAloud[59198:5782367] [claims] Claim BB0A3B69-1526-4470-B2A8-69237A161EF1 failed during preparing for uploading due to error: Error Domain=NSCocoaErrorDomain Code=260 "The file “dbdc3267e451b4caf6b59972daad48652ceca071” couldn’t be opened because there is no such file." UserInfo={NSURL=file:///Users/willwade-personal/Library/Developer/CoreSimulator/Devices/B4E7C980-0619-4FC9-BEA0-CB94CEAE849B/data/Library/Caches/com.apple.Pasteboard/eb77e5f8f043896faf63b5041f0fbd121db984dd/dbdc3267e451b4caf6b59972daad48652ceca071, NSFilePath=/Users/willwade-personal/Library/Developer/CoreSimulator/Devices/B4E7C980-0619-4FC9-BEA0-CB94CEAE849B/data/Library/Caches/com.apple.Pasteboard/eb77e5f8f043896faf63b5041f0fbd121db984dd/dbdc3267e451b4caf6b59972daad48652ceca071, NSUnderlyingError=0x600001c0a250 {Error Domain=NSPOSIXErrorDomain Code=2 "No such file or directory"}} update