I use the Fiddler proxy to debug all kinds of HTTP issues on Windows. It's great for inspecting headers and responses across multiple pages.
Is there a good HTTP debugging proxy for Mac and Linux? I found Charles, but it's $50 once the trial runs out and it crashed on me. I could use Wireshark, but it's a pain.
Mitmproxy is a useful command-line proxy tool.
It has also an user UI.
mitmweb
You can also try Proxy.app by Websecurify. It is 100% native, available from the Mac App Store.
Wireshark won't help you if you have to debug HTTPS requests (unless you can get the encryption keys for both endpoints - see the Wireshark site for details). Firebug and Tamper Data are getting close, but for thorough analysis, I sometimes like to save a recorded session. I'd recommend giving the OWASP Zed Attack Proxy (the successor of Parosproxy, which is no longer actively developed) a try. It is a Java application serving as a http(s) proxy; it provides quite a lot of features and proved to be very helpful to me in the past.
ZAP offers an easy autoconfiguration of Firefox. Bear in mind to do that on a separate (meaning: not for other browsing activities) Firefox profile: In order to intercept https, ZAP will install a new SSL certificate.
Charles is $50 as you know, but I find it to be completely worth the money. A ton of features, including SSL support.
FWIW, I've never had it crash on me.
You can use chrome:
chrome://net-internals/#events