Which API are you using ? You talk about sockets but tcp_write() is a
RAW API function which requires an application framework with callbacks.
If you don't catch the ACKs you don't free the buffers you can't send.
I may be wrong, but I think the netconn and socket API require an OS.
Can you please sniff and capture the traffic ?
PPP has a log mode (iirc) if you can't sniff the serial.
Can you please describe your scenario in terms of IP networks and
addresses plus applications ?
Can you please describe your scenario what you do in a sequential way
stating clearly what "works" and what does not ? This way we (you) can
correlate what "does not work" with what is seen on the wire.
Are you calling sys_check_timeouts() in your main loop ?
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