If you keep breaking a string trying to get it up to pitch on your cigar box guitar, try moving a gauge or too smaller. For example if you are trying to get a .012” plain steel string up to high G and it snaps, try a .011 or .010” instead. In general, smaller = higher, larger = lower in terms of strings, pitch and optimal tension. Check out our knowledgebase articles about strings to learn more!
You can also make it easy on yourself by grabbing some of string sets for cigar box guitars available from the Southbound String Company, from C. B. Gitty.