Setting and Overview
After warning the disciples that the time of his return is unknown, Jesus then exhorts them strongly to be ready for his return at any time. While human nature is to let down our guard over time, Jesus has prepared them to expect a delay before his return, but also given them signs which they will see even in their lifetime that are indications that his return can be coming soon. Matthew 24:42 opens up an inclusio that will close with 25:13, parallel commands to stay alert, which also bracket parables which will illustrate and drive home his point.

Exposition
When Jesus gives the first exhortation to “stay alert” in verse 42, there is already an indication that he is calling for more than just simple awareness. In other New Testament commands for “alertness,” we see related exhortations for prayerfulness (Colossians 4:2), standing firm (I Corinthians 16:13), and spiritual growth (Revelation 3:2.) Alertness calls for an attitude and mindset ready for engagement and action, which is then demonstrated in the illustration of a homeowner protecting his house from a thief. It is easy enough to protect the house if one knows when the thief is coming, but true readiness can protect even if the time is unknown.
Jesus then challenges his listeners to examine themselves and see which of two servants that they can identify with. In both cases, the servant is delegated authority over and responsibility for the household while the master is away, a role known as a household steward (Luke 12:41-46.) The wise servant is one who uses the time to carry out his duties faithfully and then receives the approval of the master he returns and is honored with more responsibility (Matthew 25:21-23.) In contrast, the evil servant uses the master’s absence to abuse his power for his own benefit, either assuming that the master will never return or hoping that he will have time to set things right before he does. When the master returns unexpectedly, the evil servant is punished and banished (Matthew 8:12, 22:13.)
Jesus then gives an even more in depth parable about a bridegroom and ten maidens. In the parable, he says first that five are foolish because they did not bring extra oil for their torches, and five are wise because they do. It is not certain if the foolish maidens thought that they still had time to get more oil, or that they assumed that their torches would only need to burn for a short time. Either way, when the bridegroom is delayed for a long time and then returns with no warning, all ten maidens are awakened but have different reactions to the bridegroom’s return. While all ten maidens had slept and were surprised by the return, the five wise ones had already prepared beforehand and are ready quickly to perform their duties. The five foolish ones don’t have the necessary oil, and after being rebuffed in their request for oil from the others, they are forced to go find a seller in the middle of the night. We don’t know if they are eventually successful in trying to buy the oil or not, but ultimately it is a moot point as they find themselves locked out of the banquet by the time that they return. The bridegroom’s harsh response that he does not know them connects back to Jesus’ warning at the end of the Sermon on the Mount. Ultimately, entrance into the kingdom still comes down to a relationship with Jesus and at some point it will be too late to accept his invitation (Matthew 11:28-30.)

Examination and Application
As Jesus’ disciples, we are called to be living on mission, ready at any point to answer for what we have done with the time that we have. While much attention gets paid to how soon Jesus may return, his exhortation is not to awareness but to readiness. We have been given jobs to do (Mark 13:37) and every one of us must be ready to give an account. This will we require prayer, spiritual growth, and building relationships (Titus 3:1-2, I Peter 3:15-16) as we seek to take the Gospels to the ends of the earth and make disciples of every nation (Matthew 28:18-20.)