Sending multiple files on Telegram for Android is currently broken in two related scenarios.
When multiple files are selected in a third-party app or file manager and shared to Telegram through the Android Share menu, Telegram creates a grouped file message, but the message fails to send and displays a red exclamation mark. Sending the same files one at a time works normally.
When multiple files are selected directly from Telegram's own file picker, they can be sent, but Telegram sends each file as a separate message instead of grouping them into a single file album/message as it did previously.
The attached video demonstrates the first issue using PDF files shared from Total Commander: multiple selected files fail to send, while a single selected file sends successfully.
Both problems appear to affect the handling or grouping of multiple document URIs on newer Android versions.
Steps to reproduce
Scenario 1 — Share multiple files from another app
Open a file manager or another app that can share files, such as Total Commander.
Select two or more files.
Tap Share and choose Telegram.
Select any Telegram chat or Saved Messages.
Send the files.
Observe that Telegram creates a grouped file message, but the upload/send fails with a red exclamation mark.
Repeat the same process with only one file selected.
Observe that the single file sends successfully.
Scenario 2 — Select multiple files from inside Telegram
Open any Telegram chat.
Open the attachment menu and choose File.
Select two or more files.
Send them.
Observe how the files are sent.
Current result
In Scenario 1, a grouped file message is created, but sending multiple files fails with a red exclamation mark. A single file sends successfully.
In Scenario 2, multiple files are sent as separate messages instead of being grouped into a single file album/message.
Expected result
Multiple files should be sent successfully when shared to Telegram from another app, and multiple files selected from Telegram's file picker should be grouped into a single file album/message as they were previously.
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