A prolonged journey through a barren wasteland is often viewed as a harsh punishment. However, the wandering of the Israelites actually stemmed from profound mercy and divine kindness. The primary approach among commentators is that God guided the people through an unsown, pathless, and desolate land. He provided clear direction using a pillar of cloud during the day and a pillar of fire at night. He surrounded them with clouds of glory and miraculously supplied all their physical needs.
Beyond physical protection, the kindness of the journey is found in its specific route and underlying purpose. God intentionally led the Israelites on a longer, roundabout path rather than a direct one. This detour was designed to prevent them from experiencing regret and attempting to return to Egypt [אלשיך]. The wandering and the hardships they endured were necessary to purify them. It served to uproot the corrupt beliefs they had absorbed during their time in Egypt and prepared them to learn God's ways and His teachings [מלבי״ם]. Furthermore, the specific challenges of the desert route ultimately led to a greater reward, allowing them to expand their eventual inheritance by conquering the lands of Sihon and Og [מלבי״ם].
A crucial aspect of this journey is that God led the people directly, rather than relying on a messenger. This direct guidance was an act of kindness intended to protect the Israelites from a severe mistake in their faith. If they had been led by an angel, they might have mistakenly worshipped it instead of God. Such an error would have led to their complete destruction, and ultimately, the destruction of the entire world [אלשיך].