Fae added a comment.
With regard to debugging, these examples may be of interest: 1. IA TheOakLeaf1949January1June25 <https://commons.wikimedia.org/wiki/File:The_Oak_Leaf_Vol._8_(January_1_-_June_25,_1949)_(IA_TheOakLeaf1949January1June25).pdf> 59MB, took 23 upload attempts before successful upload 2. IA asagraycorrespo00grayg <https://commons.wikimedia.org/wiki/File:Asa_Gray_correspondence._1838-1898_(inclusive)_(IA_asagraycorrespo00grayg).pdf> 1.44 GB, uploaded on first attempt It seems likely that the internal format of these two PDFs, rather than just size, is key to understanding why some will repeatedly fail to upload and not others. TASK DETAIL https://phabricator.wikimedia.org/T254459 EMAIL PREFERENCES https://phabricator.wikimedia.org/settings/panel/emailpreferences/ To: Fae Cc: Xover, eprodromou, AntiCompositeNumber, ShakespeareFan00, Dvorapa, Aklapper, pywikibot-bugs-list, Fae, Naike, CBogen, Biazzzzoo, Philoserf, CptViraj, WDoranWMF, Chambersjay, DannyS712, JKSTNK, Jony, Amorymeltzer, Conradrock, Ramsey-WMF, Sethakill, dg711, Poyekhali, Agabi10, Taiwania_Justo, Pchelolo, Ixocactus, Wong128hk, Hydriz, El_Grafo, Dinoguy1000, jayvdb, Anomie, Steinsplitter, Rxy, Jay8g, fgiunchedi, Keegan, Legoktm, Tgr
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