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There could be a few reasons why the readline() function of pyserial is experiencing a timeout after reconnecting:

1. The buffer may be full: It is possible that the buffer is full and the readline() function is unable to read any more data. In this case, you may need to clear the buffer before calling readline().

2. Connection issues: There may be connection issues between the devices, especially if they have been disconnected for a long time. Check the serial port settings, baud rate, and flow control settings.

3. Hardware issues: There may be hardware issues with the devices, such as faulty cables or a damaged serial port. You may need to replace the cables or try using a different serial port.

4. Software issues: There may be software issues with pyserial, such as a bug or compatibility issue. Try updating pyserial to the latest version or switch to a different library.

5. Timing issues: The timeout duration of the readline() function may be too short or too long. Adjust the timeout value to match the data transfer rate between the devices.

It is important to troubleshoot these issues systematically to identify and resolve the root cause of the problem.