Looking at the raw HTTP headers in the browser, I came across these HTTP errors:
HTTP 413 Request entity too large: /service/upload?fmt=extended,raw
HTTP 504 Gateway Timeout: /service/soap/NoOpRequest
I found this post related to a 413 bug from 2020:
viewtopic.php?t=67967
I don't see anywhere that clearly shows the nginx error log so I wasn't able to produce that log.
Unrelated to the above, I've expanded the log level in mailbox.log to "debug" in the log4j settings. I'll call out that these two lines appear in the successful attachment, but do not appear in the rejected attachment.
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#SUCCESSFUL ATTACHMENT
2023-10-04 11:31:06,976 DEBUG [qtp252651381-321:https://DOMAIN/service/soap/SaveDraftRequest] [name=ME@DOMAIN.TLD;mid=16;oip=192.168.0.1, 192.168.0.24;oproto=https;port=44766;ua=ZimbraWebClient - FF117 (Mac)/8.8.15_GA_3;soapId=262469e2;] mailbox - setting recent count to 0
2023-10-04 11:31:07,103 INFO [qtp252651381-140:https://DOMAIN/service/upload?fmt=extended,raw] [name=ME@DOMAIN.TLD;mid=16;oip=192.168.0.1, 192.168.0.24;oproto=https;port=44768;ua=Mozilla/5.0 (Macintosh;; Intel Mac OS X 10.15;; rv:109.0) Gecko/20100101 Firefox/117.0;] FileUploadServlet - Received plain: Upload: { accountId=xxxxxxxx, time=Wed Oct 04 11:31:07 EDT 2023, size=184242, uploadId=58e78944-cbbf-4163-9790-47ae3f3fe9e9:9815cd78-ecef-4cb3-9cad-06bf92ea359e, name=example.pdf, path=/opt/zimbra/data/tmp/upload/upload__5369f706_18afb3e3011__8000_00000093.tmp }
Here's the full log dump of the full successful debug log in mailbox.log:
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2023-10-04 11:31:06,971 DEBUG [qtp252651381-321:https://DOMAIN/service/soap/SaveDraftRequest] [name=ME@DOMAIN.TLD;mid=16;oip=192.168.0.1, 192.168.0.24;oproto=https;port=44766;ua=ZimbraWebClient - FF117 (Mac)/8.8.15_GA_3;soapId=262469e2;] mailbox - beginning operation: saveDraft
2023-10-04 11:31:06,975 DEBUG [qtp252651381-321:https://DOMAIN/service/soap/SaveDraftRequest] [name=ME@DOMAIN.TLD;mid=16;oip=192.168.0.1, 192.168.0.24;oproto=https;port=44766;ua=ZimbraWebClient - FF117 (Mac)/8.8.15_GA_3;soapId=262469e2;] mailbox - fetching new DB connection
2023-10-04 11:31:06,976 DEBUG [qtp252651381-321:https://DOMAIN/service/soap/SaveDraftRequest] [name=ME@DOMAIN.TLD;mid=16;oip=192.168.0.1, 192.168.0.24;oproto=https;port=44766;ua=ZimbraWebClient - FF117 (Mac)/8.8.15_GA_3;soapId=262469e2;] mailbox - ending operation SaveDraft
2023-10-04 11:31:06,976 DEBUG [qtp252651381-321:https://DOMAIN/service/soap/SaveDraftRequest] [name=ME@DOMAIN.TLD;mid=16;oip=192.168.0.1, 192.168.0.24;oproto=https;port=44766;ua=ZimbraWebClient - FF117 (Mac)/8.8.15_GA_3;soapId=262469e2;] mailbox - setting recent count to 0
2023-10-04 11:31:06,977 DEBUG [qtp252651381-321:https://DOMAIN/service/soap/SaveDraftRequest] [name=ME@DOMAIN.TLD;mid=16;oip=192.168.0.1, 192.168.0.24;oproto=https;port=44766;ua=ZimbraWebClient - FF117 (Mac)/8.8.15_GA_3;soapId=262469e2;] mailbox - "Drafts": updating folder counts (c28/d0/u0/du0/s1724)
2023-10-04 11:31:06,980 DEBUG [qtp252651381-321:https://DOMAIN/service/soap/SaveDraftRequest] [name=ME@DOMAIN.TLD;mid=16;oip=192.168.0.1, 192.168.0.24;oproto=https;port=44766;ua=ZimbraWebClient - FF117 (Mac)/8.8.15_GA_3;soapId=262469e2;] mailbox - clearing change
2023-10-04 11:31:06,981 DEBUG [qtp252651381-321:https://DOMAIN/service/soap/SaveDraftRequest] [name=ME@DOMAIN.TLD;mid=16;oip=192.168.0.1, 192.168.0.24;oproto=https;port=44766;ua=ZimbraWebClient - FF117 (Mac)/8.8.15_GA_3;soapId=262469e2;] mailbox - ItemAction batchSize=1000
2023-10-04 11:31:06,981 DEBUG [qtp252651381-321:https://DOMAIN/service/soap/SaveDraftRequest] [name=ME@DOMAIN.TLD;mid=16;oip=192.168.0.1, 192.168.0.24;oproto=https;port=44766;ua=ZimbraWebClient - FF117 (Mac)/8.8.15_GA_3;soapId=262469e2;] mailbox - beginning operation: setColor
2023-10-04 11:31:06,981 DEBUG [qtp252651381-321:https://DOMAIN/service/soap/SaveDraftRequest] [name=ME@DOMAIN.TLD;mid=16;oip=192.168.0.1, 192.168.0.24;oproto=https;port=44766;ua=ZimbraWebClient - FF117 (Mac)/8.8.15_GA_3;soapId=262469e2;] mailbox - ending operation ColorItem
2023-10-04 11:31:06,983 DEBUG [qtp252651381-321:https://DOMAIN/service/soap/SaveDraftRequest] [name=ME@DOMAIN.TLD;mid=16;oip=192.168.0.1, 192.168.0.24;oproto=https;port=44766;ua=ZimbraWebClient - FF117 (Mac)/8.8.15_GA_3;soapId=262469e2;] mailbox - clearing change
2023-10-04 11:31:06,983 DEBUG [qtp252651381-321:https://DOMAIN/service/soap/SaveDraftRequest] [name=ME@DOMAIN.TLD;mid=16;oip=192.168.0.1, 192.168.0.24;oproto=https;port=44766;ua=ZimbraWebClient - FF117 (Mac)/8.8.15_GA_3;soapId=262469e2;] mailbox - beginning operation: getItemById
2023-10-04 11:31:06,983 DEBUG [qtp252651381-321:https://DOMAIN/service/soap/SaveDraftRequest] [name=ME@DOMAIN.TLD;mid=16;oip=192.168.0.1, 192.168.0.24;oproto=https;port=44766;ua=ZimbraWebClient - FF117 (Mac)/8.8.15_GA_3;soapId=262469e2;] mailbox - ending operation
2023-10-04 11:31:06,983 DEBUG [qtp252651381-321:https://DOMAIN/service/soap/SaveDraftRequest] [name=ME@DOMAIN.TLD;mid=16;oip=192.168.0.1, 192.168.0.24;oproto=https;port=44766;ua=ZimbraWebClient - FF117 (Mac)/8.8.15_GA_3;soapId=262469e2;] mailbox - clearing change
2023-10-04 11:31:06,987 INFO [qtp252651381-321:https://DOMAIN/service/soap/SaveDraftRequest] [name=ME@DOMAIN.TLD;mid=16;oip=192.168.0.1, 192.168.0.24;oproto=https;port=44766;ua=ZimbraWebClient - FF117 (Mac)/8.8.15_GA_3;soapId=262469e2;] soap - SaveDraftRequest elapsed=26
2023-10-04 11:31:07,103 INFO [qtp252651381-140:https://DOMAIN/service/upload?fmt=extended,raw] [name=ME@DOMAIN.TLD;mid=16;oip=192.168.0.1, 192.168.0.24;oproto=https;port=44768;ua=Mozilla/5.0 (Macintosh;; Intel Mac OS X 10.15;; rv:109.0) Gecko/20100101 Firefox/117.0;] FileUploadServlet - Received plain: Upload: { accountId=xxxxxxxx, time=Wed Oct 04 11:31:07 EDT 2023, size=184242, uploadId=58e78944-cbbf-4163-9790-47ae3f3fe9e9:9815cd78-ecef-4cb3-9cad-06bf92ea359e, name=example.pdf, path=/opt/zimbra/data/tmp/upload/upload__5369f706_18afb3e3011__8000_00000093.tmp }
2023-10-04 11:31:07,155 DEBUG [qtp252651381-140:https://DOMAIN/service/soap/SaveDraftRequest] [name=ME@DOMAIN.TLD;mid=16;oip=192.168.0.1, 192.168.0.24;oproto=https;port=44770;ua=ZimbraWebClient - FF117 (Mac)/8.8.15_GA_3;soapId=262469e4;] mailbox - beginning operation: saveDraft
2023-10-04 11:31:07,161 DEBUG [qtp252651381-140:https://DOMAIN/service/soap/SaveDraftRequest] [name=ME@DOMAIN.TLD;mid=16;oip=192.168.0.1, 192.168.0.24;oproto=https;port=44770;ua=ZimbraWebClient - FF117 (Mac)/8.8.15_GA_3;soapId=262469e4;] mailbox - fetching new DB connection
2023-10-04 11:31:07,162 DEBUG [qtp252651381-140:https://DOMAIN/service/soap/SaveDraftRequest] [name=ME@DOMAIN.TLD;mid=16;oip=192.168.0.1, 192.168.0.24;oproto=https;port=44770;ua=ZimbraWebClient - FF117 (Mac)/8.8.15_GA_3;soapId=262469e4;] mailbox - ending operation SaveDraft
2023-10-04 11:31:07,163 DEBUG [qtp252651381-140:https://DOMAIN/service/soap/SaveDraftRequest] [name=ME@DOMAIN.TLD;mid=16;oip=192.168.0.1, 192.168.0.24;oproto=https;port=44770;ua=ZimbraWebClient - FF117 (Mac)/8.8.15_GA_3;soapId=262469e4;] mailbox - "Drafts": updating folder counts (c28/d0/u0/du0/s1724)
2023-10-04 11:31:07,172 DEBUG [qtp252651381-140:https://DOMAIN/service/soap/SaveDraftRequest] [name=ME@DOMAIN.TLD;mid=16;oip=192.168.0.1, 192.168.0.24;oproto=https;port=44770;ua=ZimbraWebClient - FF117 (Mac)/8.8.15_GA_3;soapId=262469e4;] mailbox - clearing change
2023-10-04 11:31:07,173 DEBUG [qtp252651381-140:https://DOMAIN/service/soap/SaveDraftRequest] [name=ME@DOMAIN.TLD;mid=16;oip=192.168.0.1, 192.168.0.24;oproto=https;port=44770;ua=ZimbraWebClient - FF117 (Mac)/8.8.15_GA_3;soapId=262469e4;] mailbox - ItemAction batchSize=1000
2023-10-04 11:31:07,173 DEBUG [qtp252651381-140:https://DOMAIN/service/soap/SaveDraftRequest] [name=ME@DOMAIN.TLD;mid=16;oip=192.168.0.1, 192.168.0.24;oproto=https;port=44770;ua=ZimbraWebClient - FF117 (Mac)/8.8.15_GA_3;soapId=262469e4;] mailbox - beginning operation: setColor
2023-10-04 11:31:07,173 DEBUG [qtp252651381-140:https://DOMAIN/service/soap/SaveDraftRequest] [name=ME@DOMAIN.TLD;mid=16;oip=192.168.0.1, 192.168.0.24;oproto=https;port=44770;ua=ZimbraWebClient - FF117 (Mac)/8.8.15_GA_3;soapId=262469e4;] mailbox - ending operation ColorItem
2023-10-04 11:31:07,173 DEBUG [qtp252651381-140:https://DOMAIN/service/soap/SaveDraftRequest] [name=ME@DOMAIN.TLD;mid=16;oip=192.168.0.1, 192.168.0.24;oproto=https;port=44770;ua=ZimbraWebClient - FF117 (Mac)/8.8.15_GA_3;soapId=262469e4;] mailbox - clearing change
2023-10-04 11:31:07,173 DEBUG [qtp252651381-140:https://DOMAIN/service/soap/SaveDraftRequest] [name=ME@DOMAIN.TLD;mid=16;oip=192.168.0.1, 192.168.0.24;oproto=https;port=44770;ua=ZimbraWebClient - FF117 (Mac)/8.8.15_GA_3;soapId=262469e4;] mailbox - beginning operation: getItemById
2023-10-04 11:31:07,173 DEBUG [qtp252651381-140:https://DOMAIN/service/soap/SaveDraftRequest] [name=ME@DOMAIN.TLD;mid=16;oip=192.168.0.1, 192.168.0.24;oproto=https;port=44770;ua=ZimbraWebClient - FF117 (Mac)/8.8.15_GA_3;soapId=262469e4;] mailbox - ending operation
2023-10-04 11:31:07,173 DEBUG [qtp252651381-140:https://DOMAIN/service/soap/SaveDraftRequest] [name=ME@DOMAIN.TLD;mid=16;oip=192.168.0.1, 192.168.0.24;oproto=https;port=44770;ua=ZimbraWebClient - FF117 (Mac)/8.8.15_GA_3;soapId=262469e4;] mailbox - clearing change
2023-10-04 11:31:07,182 INFO [qtp252651381-140:https://DOMAIN/service/soap/SaveDraftRequest] [name=ME@DOMAIN.TLD;mid=16;oip=192.168.0.1, 192.168.0.24;oproto=https;port=44770;ua=ZimbraWebClient - FF117 (Mac)/8.8.15_GA_3;soapId=262469e4;] soap - SaveDraftRequest elapsed=59
Here is the full log dump of the rejected attachment in mailbox.log:
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2023-10-04 11:14:36,913 DEBUG [qtp252651381-148:https://DOMAIN/service/soap/SaveDraftRequest] [name=ME@DOMAIN.TLD;mid=16;oip=192.168.0.1, 192.168.0.24;oproto=https;port=43552;ua=ZimbraWebClient - FF117 (Mac)/8.8.15_GA_3;soapId=26246829;] mailbox - beginning operation: saveDraft
2023-10-04 11:14:36,917 DEBUG [qtp252651381-148:https://DOMAIN/service/soap/SaveDraftRequest] [name=ME@DOMAIN.TLD;mid=16;oip=192.168.0.1, 192.168.0.24;oproto=https;port=43552;ua=ZimbraWebClient - FF117 (Mac)/8.8.15_GA_3;soapId=26246829;] mailbox - fetching new DB connection
2023-10-04 11:14:36,918 DEBUG [qtp252651381-148:https://DOMAIN/service/soap/SaveDraftRequest] [name=ME@DOMAIN.TLD;mid=16;oip=192.168.0.1, 192.168.0.24;oproto=https;port=43552;ua=ZimbraWebClient - FF117 (Mac)/8.8.15_GA_3;soapId=26246829;] mailbox - ending operation SaveDraft
2023-10-04 11:14:36,919 DEBUG [qtp252651381-148:https://DOMAIN/service/soap/SaveDraftRequest] [name=ME@DOMAIN.TLD;mid=16;oip=192.168.0.1, 192.168.0.24;oproto=https;port=43552;ua=ZimbraWebClient - FF117 (Mac)/8.8.15_GA_3;soapId=26246829;] mailbox - "Drafts": updating folder counts (c28/d0/u0/du0/s1724)
2023-10-04 11:14:36,925 DEBUG [qtp252651381-148:https://DOMAIN/service/soap/SaveDraftRequest] [name=ME@DOMAIN.TLD;mid=16;oip=192.168.0.1, 192.168.0.24;oproto=https;port=43552;ua=ZimbraWebClient - FF117 (Mac)/8.8.15_GA_3;soapId=26246829;] mailbox - clearing change
2023-10-04 11:14:36,925 DEBUG [qtp252651381-148:https://DOMAIN/service/soap/SaveDraftRequest] [name=ME@DOMAIN.TLD;mid=16;oip=192.168.0.1, 192.168.0.24;oproto=https;port=43552;ua=ZimbraWebClient - FF117 (Mac)/8.8.15_GA_3;soapId=26246829;] mailbox - ItemAction batchSize=1000
2023-10-04 11:14:36,925 DEBUG [qtp252651381-148:https://DOMAIN/service/soap/SaveDraftRequest] [name=ME@DOMAIN.TLD;mid=16;oip=192.168.0.1, 192.168.0.24;oproto=https;port=43552;ua=ZimbraWebClient - FF117 (Mac)/8.8.15_GA_3;soapId=26246829;] mailbox - beginning operation: setColor
2023-10-04 11:14:36,925 DEBUG [qtp252651381-148:https://DOMAIN/service/soap/SaveDraftRequest] [name=ME@DOMAIN.TLD;mid=16;oip=192.168.0.1, 192.168.0.24;oproto=https;port=43552;ua=ZimbraWebClient - FF117 (Mac)/8.8.15_GA_3;soapId=26246829;] mailbox - ending operation ColorItem
2023-10-04 11:14:36,929 DEBUG [qtp252651381-148:https://DOMAIN/service/soap/SaveDraftRequest] [name=ME@DOMAIN.TLD;mid=16;oip=192.168.0.1, 192.168.0.24;oproto=https;port=43552;ua=ZimbraWebClient - FF117 (Mac)/8.8.15_GA_3;soapId=26246829;] mailbox - clearing change
2023-10-04 11:14:36,929 DEBUG [qtp252651381-148:https://DOMAIN/service/soap/SaveDraftRequest] [name=ME@DOMAIN.TLD;mid=16;oip=192.168.0.1, 192.168.0.24;oproto=https;port=43552;ua=ZimbraWebClient - FF117 (Mac)/8.8.15_GA_3;soapId=26246829;] mailbox - beginning operation: getItemById
2023-10-04 11:14:36,929 DEBUG [qtp252651381-148:https://DOMAIN/service/soap/SaveDraftRequest] [name=ME@DOMAIN.TLD;mid=16;oip=192.168.0.1, 192.168.0.24;oproto=https;port=43552;ua=ZimbraWebClient - FF117 (Mac)/8.8.15_GA_3;soapId=26246829;] mailbox - ending operation
2023-10-04 11:14:36,929 DEBUG [qtp252651381-148:https://DOMAIN/service/soap/SaveDraftRequest] [name=ME@DOMAIN.TLD;mid=16;oip=192.168.0.1, 192.168.0.24;oproto=https;port=43552;ua=ZimbraWebClient - FF117 (Mac)/8.8.15_GA_3;soapId=26246829;] mailbox - clearing change
2023-10-04 11:14:36,933 INFO [qtp252651381-148:https://DOMAIN/service/soap/SaveDraftRequest] [name=ME@DOMAIN.TLD;mid=16;oip=192.168.0.1, 192.168.0.24;oproto=https;port=43552;ua=ZimbraWebClient - FF117 (Mac)/8.8.15_GA_3;soapId=26246829;] soap - SaveDraftRequest elapsed=28
2023-10-04 11:14:37,040 DEBUG [qtp252651381-132:https://DOMAIN/service/soap/SaveDraftRequest] [name=ME@DOMAIN.TLD;mid=16;oip=192.168.0.1, 192.168.0.24;oproto=https;port=43554;ua=ZimbraWebClient - FF117 (Mac)/8.8.15_GA_3;soapId=2624682b;] mailbox - beginning operation: saveDraft
2023-10-04 11:14:37,043 DEBUG [qtp252651381-132:https://DOMAIN/service/soap/SaveDraftRequest] [name=ME@DOMAIN.TLD;mid=16;oip=192.168.0.1, 192.168.0.24;oproto=https;port=43554;ua=ZimbraWebClient - FF117 (Mac)/8.8.15_GA_3;soapId=2624682b;] mailbox - fetching new DB connection
2023-10-04 11:14:37,043 DEBUG [qtp252651381-132:https://DOMAIN/service/soap/SaveDraftRequest] [name=ME@DOMAIN.TLD;mid=16;oip=192.168.0.1, 192.168.0.24;oproto=https;port=43554;ua=ZimbraWebClient - FF117 (Mac)/8.8.15_GA_3;soapId=2624682b;] mailbox - ending operation SaveDraft
2023-10-04 11:14:37,043 DEBUG [qtp252651381-132:https://DOMAIN/service/soap/SaveDraftRequest] [name=ME@DOMAIN.TLD;mid=16;oip=192.168.0.1, 192.168.0.24;oproto=https;port=43554;ua=ZimbraWebClient - FF117 (Mac)/8.8.15_GA_3;soapId=2624682b;] mailbox - "Drafts": updating folder counts (c28/d0/u0/du0/s1724)
2023-10-04 11:14:37,046 DEBUG [qtp252651381-132:https://DOMAIN/service/soap/SaveDraftRequest] [name=ME@DOMAIN.TLD;mid=16;oip=192.168.0.1, 192.168.0.24;oproto=https;port=43554;ua=ZimbraWebClient - FF117 (Mac)/8.8.15_GA_3;soapId=2624682b;] mailbox - clearing change
2023-10-04 11:14:37,046 DEBUG [qtp252651381-132:https://DOMAIN/service/soap/SaveDraftRequest] [name=ME@DOMAIN.TLD;mid=16;oip=192.168.0.1, 192.168.0.24;oproto=https;port=43554;ua=ZimbraWebClient - FF117 (Mac)/8.8.15_GA_3;soapId=2624682b;] mailbox - ItemAction batchSize=1000
2023-10-04 11:14:37,046 DEBUG [qtp252651381-132:https://DOMAIN/service/soap/SaveDraftRequest] [name=ME@DOMAIN.TLD;mid=16;oip=192.168.0.1, 192.168.0.24;oproto=https;port=43554;ua=ZimbraWebClient - FF117 (Mac)/8.8.15_GA_3;soapId=2624682b;] mailbox - beginning operation: setColor
2023-10-04 11:14:37,046 DEBUG [qtp252651381-132:https://DOMAIN/service/soap/SaveDraftRequest] [name=ME@DOMAIN.TLD;mid=16;oip=192.168.0.1, 192.168.0.24;oproto=https;port=43554;ua=ZimbraWebClient - FF117 (Mac)/8.8.15_GA_3;soapId=2624682b;] mailbox - ending operation ColorItem
2023-10-04 11:14:37,047 DEBUG [qtp252651381-132:https://DOMAIN/service/soap/SaveDraftRequest] [name=ME@DOMAIN.TLD;mid=16;oip=192.168.0.1, 192.168.0.24;oproto=https;port=43554;ua=ZimbraWebClient - FF117 (Mac)/8.8.15_GA_3;soapId=2624682b;] mailbox - clearing change
2023-10-04 11:14:37,047 DEBUG [qtp252651381-132:https://DOMAIN/service/soap/SaveDraftRequest] [name=ME@DOMAIN.TLD;mid=16;oip=192.168.0.1, 192.168.0.24;oproto=https;port=43554;ua=ZimbraWebClient - FF117 (Mac)/8.8.15_GA_3;soapId=2624682b;] mailbox - beginning operation: getItemById
2023-10-04 11:14:37,047 DEBUG [qtp252651381-132:https://DOMAIN/service/soap/SaveDraftRequest] [name=ME@DOMAIN.TLD;mid=16;oip=192.168.0.1, 192.168.0.24;oproto=https;port=43554;ua=ZimbraWebClient - FF117 (Mac)/8.8.15_GA_3;soapId=2624682b;] mailbox - ending operation
2023-10-04 11:14:37,047 DEBUG [qtp252651381-132:https://DOMAIN/service/soap/SaveDraftRequest] [name=ME@DOMAIN.TLD;mid=16;oip=192.168.0.1, 192.168.0.24;oproto=https;port=43554;ua=ZimbraWebClient - FF117 (Mac)/8.8.15_GA_3;soapId=2624682b;] mailbox - clearing change
2023-10-04 11:14:37,051 INFO [qtp252651381-132:https://DOMAIN/service/soap/SaveDraftRequest] [name=ME@DOMAIN.TLD;mid=16;oip=192.168.0.1, 192.168.0.24;oproto=https;port=43554;ua=ZimbraWebClient - FF117 (Mac)/8.8.15_GA_3;soapId=2624682b;] soap - SaveDraftRequest elapsed=18