Saint Benedict loves obedience. Besides writing about it in previous chapters (as well as in future chapters!) he dedicates the entirety of chapter five on it. However, Saint Benedict’s writings on this topic do come across as a little worrisome. He demands nothing less than blind obedience from his monks. The first sentence of chapter five is “The first degree of humility is obedience without delay” (Saint Benedict pg. 23). Monks are supposed to be humble so it’s natural that he would talk about how to be humble (he goes more into detail in chapter seven), but Saint Benedict takes this obsession with obedience a bit too far:
“[A]s soon as anything is ordered by the superior, suffer no more delay in doing it than if it had been commanded by God Himself.” (Saint Benedict pg. 23)
Institution of a monk | BL Royal 11 D IX, f. 195 | Source: Picryl.com
One problem with this is that the superiors are human. Their commands may very well be dangerous. (And even God tried to get Abraham to kill his own son.) To make matters even more problematic, Saint Benedict wants his monks to obey while keeping in mind their “fear of hell or…the glory of life everlasting” (Saint Benedict pg. 23).
In Terrence G. Kardong’s translation of The Rule of Saint Benedict, he comments that this chapter “may appear to call for absolute ‘militaristic’ obedience…this is a false impression” (Kardong). He goes on to claim that “the abbot must conform to the high standards” (Kardong) previously set out by The Rule and if he doesn’t, there can be consequences. Kardong is extremely optimistic about how often people, the Church especially, actually follow high standards. I think it’s common knowledge that people in charge take advantage of their power. Corruption in the Catholic Church isn’t a modern-day phenomenon either. (There is an entire era of the papacy that is called the pornocracy due to its corruption.)
Saint Benedict is aware that not every monk will want to do what he is told. (And perhaps what he is told to do isn’t a result of corruption, it’s just something the monk doesn’t want to do.) Saint Benedict is also aware that when people have to do things they don’t want to, they complain, even if God loves blind obedience. As a result, he spends one-third of the chapter (which is only three paragraphs) telling his reader not to complain:
“But this very obedience will then only be acceptable to God and sweet to men, if what is commanded be done not fearfully, tardily, nor coldly, now with murmuring, nor with answer, showing unwillingness.” (Saint Benedict pg. 24)
(I will note that “murmuring” here means grumbling or complaining.)
Finally, Saint Benedict says that even if the reader does obey his superiors, God only accepts this obedience if he doesn’t complain while he does the thing he was asked to do. I do find it interesting that Saint Benedict goes into so much detail when telling his monks to stop whining. Perhaps he was sick and tired of listening to his own monks complain?
Main Source:
The Rule of Saint Benedict, With Explanatory Notes. Ichthus Publications.
(I bought my copy of The Rule of Saint Benedict on Amazon. You can purchase my edition of it here.)
Other Sources:
Benedictus, and Terrence G. Kardong. Benedicts Rule: a Translation and Commentary. Liturgical Press, 1996.
(You can find part of this book here.)
The Mediaeval Monk 
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