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I'm a member of the Pinguem.ru competition on finding errors in open source projects. A bug, found using PVS-Studio.
There are two errors (or misprints), you're checking hSession after calling InternetConnect and HttpOpenRequest in place of the checking of hConnection and hRequest.
Therefore, if there will be unavailable UPLOAD_SERVER (upload.gyazo.com) or if there will be failed post request to it (maybe wrong answer from this server), then you will get null hConnection and/or hRequest and the application will crashes.
Please, apply these changes, because it is real bug.
V547 Expression '0 == hSession' is always false. gyazowin.cpp 863
V547 Expression '0 == hSession' is always false. gyazowin.cpp 873