We're seeing similar reports from our own users, most of whom have reported this started occurring right after they updated their version of iOS (starting around 13.3.1). Most users are working around it by reinstalling the app, but this is far from ideal.This is a pretty big showstopper given the app crashes immediately on launch and there are no crash reports left behind indicating what the problem might be.
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I can confirm this issue is still occurring for us on iOS 14.2 and is exactly as you described. Our share extension does not show up in the share sheet the first time you tap the share button. But if you dismiss the sheet and tap the share button again, then it will appear the second time. Sounds like it might be a iOS or Safari bug.
Interestingly enough a very similar bug was introduced in macOS Catalina 10.15 which was ultimately fixed in 10.15.4. With that bug, share extensions that used the NSExtensionJavaScriptPreprocessingFile key simply didn't appear at all.
This appears to be randomly happening again. Curious if anyone else has been experiencing this problem lately. Found the following related logs in the Console:
default 15:39:49.352585-1000 storeuid <StoreKitClient: 0x7f8898d2d820>: Using active account. Sandbox: 1, receipt exists: NO, receipt is stub: NO
default 15:39:49.354734-1000 commerce storeuid[552] starting request app-receipt-create
default 15:39:49.455240-1000 commerce <CKStoreRequest: 0x7f94a1f64e10> https://p100-sandbox.itunes.apple.com/WebObjects/MZFinance.woa/wa/createAppReceipt
default 15:39:49.877166-1000 commerce StoreSession: StatusCode: 200; <private>; Environment: SB-MR; URL: https://p100-sandbox.itunes.apple.com/WebObjects/MZFinance.woa/wa/createAppReceipt
error 15:39:49.879812-1000 storeuid <ReceiptRefreshRequest: 0x7f889a1616e0>: No receipt data in response
error 15:39:49.879883-1000 storeuid <ReceiptRefreshRequest: 0x7f889a1616e0>: Error fetching receipt for X - Error Domain=com.apple.commerce.client Code=500 "(null)"
default 15:39:49.880675-1000 storelegacy StoreLegacy: Failed to renew receipt for application at path X : 'The operation couldn’t be completed. (com.apple.commerce.client error 500.)'
error 15:39:49.930396-1000 diagnostics_agent Invalid receipt [0 bytes]