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Sentry CLI crashes when running debug-files upload #1746

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Description

Version: 2.20.7 (bundled in the .NET SDK: getsentry/sentry-dotnet#2604)

Command:

SENTRY_LOG_LEVEL=debug /Users/bruno/git/sentry-dotnet/tools/sentry-cli/2.20.7/sentry-cli-Darwin-arm64 debug-files upload --org sentry-sdks --project sentry-dotnet -t pdb -t portablepdb bin/Debug/net7.0-macos/osx-x64/

Output (list of DLLs trimmed from log, but complete directory available on Google Drive for Sentry employees):

bruno@DHPKTVF22X Sentry.Testing.CrashableApp % SENTRY_LOG_LEVEL=debug /Users/bruno/git/sentry-dotnet/tools/sentry-cli/2.20.7/sentry-cli-Darwin-arm64 debug-files upload --org sentry-sdks --project sentry-dotnet -t pdb -t portablepdb bin/Debug/net7.0-macos/osx-x64/
  INFO    2023-09-16 17:30:56.198016 -04:00 Loaded config from /Users/bruno/.sentryclirc
  DEBUG   2023-09-16 17:30:56.198306 -04:00 sentry-cli version: 2.20.7, platform: "darwin", architecture: "arm64"
  INFO    2023-09-16 17:30:56.198313 -04:00 sentry-cli was invoked with the following command line: "/Users/bruno/git/sentry-dotnet/tools/sentry-cli/2.20.7/sentry-cli-Darwin-arm64" "debug-files" "upload" "--org" "sentry-sdks" "--project" "sentry-dotnet" "-t" "pdb" "-t" "portablepdb" "bin/Debug/net7.0-macos/osx-x64/"
  INFO    2023-09-16 17:30:56.198320 -04:00 Issuing a command for Organization: sentry-sdks Project: sentry-dotnet
  DEBUG   2023-09-16 17:30:56.198559 -04:00 request GET https://sentry.io/api/0/organizations/sentry-sdks/chunk-upload/
  DEBUG   2023-09-16 17:30:56.198566 -04:00 using token authentication
  DEBUG   2023-09-16 17:30:56.198570 -04:00 retry number 0, max retries: 0
  DEBUG   2023-09-16 17:30:56.264535 -04:00 > GET /api/0/organizations/sentry-sdks/chunk-upload/ HTTP/1.1
  DEBUG   2023-09-16 17:30:56.264555 -04:00 > Host: sentry.io
  DEBUG   2023-09-16 17:30:56.264557 -04:00 > Accept: */*
  DEBUG   2023-09-16 17:30:56.264560 -04:00 > Connection: TE
  DEBUG   2023-09-16 17:30:56.264562 -04:00 > TE: gzip
  DEBUG   2023-09-16 17:30:56.264564 -04:00 > User-Agent: sentry-cli/2.20.7
  DEBUG   2023-09-16 17:30:56.264734 -04:00 > Authorization: Bearer cd519429***
  DEBUG   2023-09-16 17:30:56.370816 -04:00 < HTTP/1.1 200 OK
  DEBUG   2023-09-16 17:30:56.370859 -04:00 < server: nginx
  DEBUG   2023-09-16 17:30:56.370869 -04:00 < date: Sat, 16 Sep 2023 21:30:56 GMT
  DEBUG   2023-09-16 17:30:56.370879 -04:00 < content-type: application/json
  DEBUG   2023-09-16 17:30:56.370888 -04:00 < Content-Length: 342
  DEBUG   2023-09-16 17:30:56.370903 -04:00 < allow: GET, POST, HEAD, OPTIONS
  DEBUG   2023-09-16 17:30:56.370911 -04:00 < access-control-allow-methods: GET, POST, HEAD, OPTIONS
  DEBUG   2023-09-16 17:30:56.370935 -04:00 < access-control-allow-headers: X-Sentry-Auth, X-Requested-With, Origin, Accept, Content-Type, Authentication, Authorization, Content-Encoding, sentry-trace, baggage, X-CSRFToken
  DEBUG   2023-09-16 17:30:56.370944 -04:00 < access-control-expose-headers: X-Sentry-Error, Retry-After
  DEBUG   2023-09-16 17:30:56.370956 -04:00 < access-control-allow-origin: *
  DEBUG   2023-09-16 17:30:56.370964 -04:00 < x-sentry-rate-limit-remaining: 199
  DEBUG   2023-09-16 17:30:56.370971 -04:00 < x-sentry-rate-limit-limit: 200
  DEBUG   2023-09-16 17:30:56.370978 -04:00 < x-sentry-rate-limit-reset: 1694899857
  DEBUG   2023-09-16 17:30:56.370986 -04:00 < x-sentry-rate-limit-concurrentremaining: 199
  DEBUG   2023-09-16 17:30:56.370993 -04:00 < x-sentry-rate-limit-concurrentlimit: 200
  DEBUG   2023-09-16 17:30:56.371001 -04:00 < vary: Accept-Language, Cookie
  DEBUG   2023-09-16 17:30:56.371008 -04:00 < content-language: en
  DEBUG   2023-09-16 17:30:56.371020 -04:00 < x-frame-options: deny
  DEBUG   2023-09-16 17:30:56.372431 -04:00 < x-content-type-options: nosniff
  DEBUG   2023-09-16 17:30:56.372447 -04:00 < x-xss-protection: 1; mode=block
  DEBUG   2023-09-16 17:30:56.372460 -04:00 < content-security-policy: frame-ancestors 'self' *.sentry.io; img-src * blob: data:; script-src 'self' 'unsafe-inline' 'report-sample' 'unsafe-eval' s1.sentry-cdn.com js.sentry-cdn.com browser.sentry-cdn.com statuspage-production.s3.amazonaws.com static.zdassets.com aui-cdn.atlassian.com connect-cdn.atl-paas.net js.stripe.com ssl.google-analytics.com 'strict-dynamic' cdn.pendo.io data.pendo.io pendo-io-static.storage.googleapis.com pendo-static-5634074999128064.storage.googleapis.com; object-src 'self'; default-src *; base-uri 'none'; font-src * data:; connect-src *; style-src * 'unsafe-inline'; report-uri https://o1.ingest.sentry.io/api/54785/security/?sentry_key=f724a8a027db45f5b21507e7142ff78e&sentry_release=f377415bfd7bcdf04185405cf7c9fb77e42cbcef
  DEBUG   2023-09-16 17:30:56.374630 -04:00 < x-envoy-attempt-count: 1
  DEBUG   2023-09-16 17:30:56.374646 -04:00 < x-envoy-upstream-service-time: 65
  DEBUG   2023-09-16 17:30:56.374654 -04:00 < x-served-by: getsentry-web-default-common-production-c4d45b4f4-h8fc8
  DEBUG   2023-09-16 17:30:56.374662 -04:00 < x-served-by: frontend-default-5494b6bc88-2z5cl
  DEBUG   2023-09-16 17:30:56.374671 -04:00 < strict-transport-security: max-age=31536000; includeSubDomains; preload
  DEBUG   2023-09-16 17:30:56.374678 -04:00 < via: 1.1 google
  DEBUG   2023-09-16 17:30:56.374686 -04:00 < Alt-Svc: h3=":443"; ma=2592000,h3-29=":443"; ma=2592000
  DEBUG   2023-09-16 17:30:56.374771 -04:00 response status: 200
  DEBUG   2023-09-16 17:30:56.375485 -04:00 body: {"url":"organizations/sentry-sdks/chunk-upload/","chunkSize":8388608,"chunksPerRequest":64,"maxFileSize":2147483648,"maxRequestSize":33554432,"concurrency":8,"hashAlgorithm":"sha1","compression":["gzip"],"accept":["debug_files","release_files","pdbs","sources","bcsymbolmaps","il2cpp","portablepdbs","artifact_bundles","artifact_bundles_v2"]}
  DEBUG   2023-09-16 17:30:56.376461 -04:00 searching location bin/Debug/net7.0-macos/osx-x64/
  DEBUG   2023-09-16 17:30:56.377058 -04:00 trying to process Microsoft.CSharp.dll
  DEBUG   2023-09-16 17:30:56.377104 -04:00 trying to parse dif Microsoft.CSharp.dll
  DEBUG   2023-09-16 17:30:56.377866 -04:00 skipping Microsoft.CSharp.dll because of format
  DEBUG   2023-09-16 17:30:56.378086 -04:00 trying to process System.Web.dll
  DEBUG   2023-09-16 17:30:56.378123 -04:00 trying to parse dif System.Web.dll
  DEBUG   2023-09-16 17:30:56.378587 -04:00 skipping System.Web.dll because of format
  DEBUG   2023-09-16 17:30:56.378733 -04:00 trying to process System.Diagnostics.Contracts.dll
  DEBUG   2023-09-16 17:30:56.378767 -04:00 trying to parse dif System.Diagnostics.Contracts.dll
  DEBUG   2023-09-16 17:30:56.379003 -04:00 skipping System.Diagnostics.Contracts.dll because of format
  DEBUG   2023-09-16 17:30:56.379123 -04:00 trying to process System.ServiceModel.Web.dll
  DEBUG   2023-09-16 17:30:56.380806 -04:00 trying to parse dif System.ServiceModel.Web.dll
  DEBUG   2023-09-16 17:30:56.381084 -04:00 skipping System.ServiceModel.Web.dll because of format
  DEBUG   2023-09-16 17:30:56.381465 -04:00 trying to process System.Diagnostics.FileVersionInfo.dll
  DEBUG   2023-09-16 17:30:56.381501 -04:00 trying to parse dif System.Diagnostics.FileVersionInfo.dll
  DEBUG   2023-09-16 17:30:56.381638 -04:00 skipping System.Diagnostics.FileVersionInfo.dll because of format
  DEBUG   2023-09-16 17:30:56.381764 -04:00 trying to process System.Runtime.Intrinsics.dll
  DEBUG   2023-09-16 17:30:56.381798 -04:00 trying to parse dif System.Runtime.Intrinsics.dll
  DEBUG   2023-09-16 17:30:56.382031 -04:00 skipping System.Runtime.Intrinsics.dll because of format
  DEBUG   2023-09-16 17:30:56.382446 -04:00 trying to process System.Net.Security.dll
  DEBUG   2023-09-16 17:30:56.387627 -04:00 trying to parse dif System.Net.Security.dll.....
  DEBUG   2023-09-16 17:30:56.450578 -04:00 trying to process Microsoft.macOS.dll
  DEBUG   2023-09-16 17:30:56.450588 -04:00 trying to parse dif Microsoft.macOS.dll
  DEBUG   2023-09-16 17:30:56.450663 -04:00 skipping Microsoft.macOS.dll because of format
  DEBUG   2023-09-16 17:30:56.450704 -04:00 trying to process System.Diagnostics.StackTrace.dll
  DEBUG   2023-09-16 17:30:56.450926 -04:00 trying to parse dif System.Diagnostics.StackTrace.dll
  DEBUG   2023-09-16 17:30:56.450966 -04:00 skipping System.Diagnostics.StackTrace.dll because of format
  DEBUG   2023-09-16 17:30:56.451004 -04:00 trying to process System.Security.dll
  DEBUG   2023-09-16 17:30:56.451013 -04:00 trying to parse dif System.Security.dll
  DEBUG   2023-09-16 17:30:56.451319 -04:00 skipping System.Security.dll because of format
  DEBUG   2023-09-16 17:30:56.451360 -04:00 trying to process System.Reflection.DispatchProxy.dll
  DEBUG   2023-09-16 17:30:56.451369 -04:00 trying to parse dif System.Reflection.DispatchProxy.dll
  DEBUG   2023-09-16 17:30:56.451408 -04:00 skipping System.Reflection.DispatchProxy.dll because of format
  DEBUG   2023-09-16 17:30:56.451603 -04:00 trying to process libclrjit.dylib
  DEBUG   2023-09-16 17:30:56.451725 -04:00 trying to process Sentry.Testing.CrashableApp.app/Contents/MacOS/Sentry.Testing.CrashableApp
  DEBUG   2023-09-16 17:30:56.451853 -04:00 trying to process Sentry.Testing.CrashableApp.app/Contents/MonoBundle/Microsoft.CSharp.dll
  DEBUG   2023-09-16 17:30:56.451863 -04:00 trying to parse dif Sentry.Testing.CrashableApp.app/Contents/MonoBundle/Microsoft.CSharp.dll
  DEBUG   2023-09-16 17:30:56.451969 -04:00 skipping Sentry.Testing.CrashableApp.app/Contents/MonoBundle/Microsoft.CSharp.dll because of format
  DEBUG   2023-09-16 17:30:56.452007 -04:00 trying to process Sentry.Testing.CrashableApp.app/Contents/MonoBundle/System.Web.dll
  DEBUG   2023-09-16 17:30:56.452016 -04:00 trying to parse dif Sentry.Testing.CrashableApp.app/Contents/MonoBundle/System.Web.dll
  DEBUG   2023-09-16 17:30:56.452298 -04:00 skipping Sentry.Testing.CrashableApp.app/Contents/MonoBundle/System.Web.dll because of format
  DEBUG   2023-09-16 17:30:56.452335 -04:00 trying to process Sentry.Testing.CrashableApp.app/Contents/MonoBundle/System.Diagnostics.Contracts.dll
  DEBUG   2023-09-16 17:30:56.452344 -04:00 trying to parse dif Sentry.Testing.CrashableApp.app/Contents/MonoBundle/System.Diagnostics.Contracts.dll
  DEBUG   2023-09-16 17:30:56.452558 -04:00 skipping Sentry.Testing.CrashableApp.app/Contents/MonoBundle/System.Diagnostics.Contracts.dll because of format
  DEBUG   2023-09-16 17:30:56.452594 -04:00 trying to process Sentry.Testing.CrashableApp.app/Contents/MonoBundle/System.ServiceModel.Web.dll
  DEBUG   2023-09-16 17:30:56.452603 -04:00 trying to parse dif Sentry.Testing.CrashableApp.app/Contents/MonoBundle/System.ServiceModel.Web.dll
  DEBUG   2023-09-16 17:30:56.452822 -04:00 skipping Sentry.Testing.CrashableApp.app/Contents/MonoBundle/System.ServiceModel.Web.dll because of format
  DEBUG   2023-09-16 17:30:56.452858 -04:00 trying to process Sentry.Testing.CrashableApp.app/Contents/MonoBundle/System.Diagnostics.FileVersionInfo.dll
  DEBUG   2023-09-16 17:30:56.452867 -04:00 trying to parse dif Sentry.Testing.CrashableApp.app/Contents/MonoBundle/System.Diagnostics.FileVersionInfo.dll
  DEBUG   2023-09-16 17:30:56.453052 -04:00 skipping Sentry.Testing.CrashableApp.app/Contents/MonoBundle/System.Diagnostics.FileVersionInfo.dll because of format
  DEBUG   2023-09-16 17:30:56.453086 -04:00 trying to process Sentry.Testing.CrashableApp.app/Contents/MonoBundle/System.Runtime.Intrinsics.dll
  DEBUG   2023-09-16 17:30:56.459538 -04:00 skipping Sentry.Testing.CrashableApp.app/Contents/MonoBundle/System.Xml.XmlDocument.dll because of format
  DEBUG   2023-09-16 17:30:56.459572 -04:00 trying to process Sentry.Testing.CrashableApp.app/Contents/MonoBundle/System.Configuration.dll
  DEBUG   2023-09-16 17:30:56.459694 -04:00 trying to parse dif Sentry.Testing.CrashableApp.app/Contents/MonoBundle/System.Configuration.dll
  DEBUG   2023-09-16 17:30:56.459764 -04:00 skipping Sentry.Testing.CrashableApp.app/Contents/MonoBundle/System.Configuration.dll because of format
  DEBUG   2023-09-16 17:30:56.459802 -04:00 trying to process Sentry.Testing.CrashableApp.app/Contents/MonoBundle/System.Resources.Writer.dll
  DEBUG   2023-09-16 17:30:56.459925 -04:00 trying to parse dif Sentry.Testing.CrashableApp.app/Contents/MonoBundle/System.Resources.Writer.dll
  DEBUG   2023-09-16 17:30:56.459965 -04:00 skipping Sentry.Testing.CrashableApp.app/Contents/MonoBundle/System.Resources.Writer.dll because of format
  DEBUG   2023-09-16 17:30:56.460 -04:00 trying to process Sentry.Testing.CrashableApp.app/Contents/MonoBundle/System.Console.dll
  DEBUG   2023-09-16 17:30:56.460148 -04:00 trying to parse dif Sentry.Testing.CrashableApp.app/Contents/MonoBundle/System.Console.dll
  DEBUG   2023-09-16 17:30:56.460188 -04:00 skipping Sentry.Testing.CrashableApp.app/Contents/MonoBundle/System.Console.dll because of format
  DEBUG   2023-09-16 17:30:56.460224 -04:00 trying to process Sentry.Testing.CrashableApp.app/Contents/MonoBundle/libcoreclr.dylib
⠁ Searching for debug symbol files...
  found 2 Sentry.Testing.CrashableApp.app/Contents/MonoBundle/System.Console.dll
zsh: killed     SENTRY_LOG_LEVEL=debug  debug-files upload --org sentry-sdks --project  -t pd
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