So what’s going on here? With John. (And, yes, the rest of the chapter is applicable.)This is of course Matthew 11:1-6, for those who prefer the ESV popup. In the interest of promoting better Bible reading, here’s my answer:
11:1 When Jesus had finished instructing his twelve disciples, he went on from there to teach and preach in their cities.
2 Now when John heard in prison about the deeds of the Christ, he sent word by his disciples 3 and said to him, “Are you the one who is to come, or shall we look for another?” 4 And Jesus answered them, “Go and tell John what you hear and see: 5 the blind receive their sight and the lame walk, lepers  are cleansed and the deaf hear, and the dead are raised up, and the poor have good news preached to them. 6 And blessed is the one who is not offended by me.”
 John’s in prison.
 John is dispatching his own disciples to Christ.
 John is a little put off by having to serve prison time while Christ is free to walk around all of Judea.
And why not? Which prophet didn’t give God a little sassy-mouth with a side of angry-eyebrow for having to suffer for the sake of being the divine messenger? Elijah sure did – and that was after seeing the prophets of Baal burned while their god was not listening in the potty. (1 Kings 18:27; 1 Kings 19:14) And let’s not bring up Jonah again, yes? So John here wants to know if the Christ is come – and, of course, that the captives will be delivered, starting with the one who was a voice crying out in the wilderness – or what.
And I think iMonk’s point in asking is this: if John is allowed a little doubt, isn’t everyone allowed a little doubt? That would make sense in the personal context of the barkeep. If he has a broader question, I’d be willing to field that, but here’s where I think that original thought goes.
The question has to be, “was John allowed a little doubt, or was John rebuked for having a little doubt?” Because Jesus doesn’t say to John, “Cousin, I’m sorry you are having a hard day and I’ll try to make it up to you.” What Jesus says – and I’d compare this to what Jesus says over and over to the Pharisees who keep demanding a sign, or that Jesus spell it out about this Messiah thing – is, “John, these are the signs of the times [with the implication that you know what they mean], and if you have to suffer a little for my sake, count it as a blessing and not as an offense.”
Jesus tells John that doubt is not warranted, and that his concerns – like the concerns of the Prophets before him – ought to be weighed against what he knows for certain to be true. And because John is John – who saw the spirit descend like a dove, and who called Jesus “the Lamb of God who takes away the sins of the world” – Jesus doesn’t pronounce the 7 woes upon him for being a malcontent and an unbeliever. But at the same time, Jesus also tells him flatly that he shouldn’t be doubting what God is about to do.
And I think that’s a great way to set up a Good Friday post, so I’ll leave it at that for the day.