When is the shadow the largest?

Shadows are longest in the early morning and late afternoon/early evening when the sun appears low in the sky. As the Earth rotates on its axis, the sun hits each location in the morning at an angle. This becomes more vertical as the sun appears to pass more directly overhead around noon.

When is the shadow the darkest?

The closer the object is to the surface, the darker and more definite its shadow becomes.

When God’s glory is felt most on this world it is.

Closer to the beginning and the end of times (late afternoon/early evening).

When he is closer to you.

These are also the times when the darkness is felt the most.

Even when I must walk through the darkest valley,

I fear no danger,

for you are with me;

your rod and your staff reassure me. (Psalm 23:4)

גַּ֤ם כִּֽי־אֵלֵ֨ךְ בְּגֵ֪יא צַלְמָ֡וֶת

  לֹא־אִ֘ירָ֤א רָ֗ע

  כִּי־אַתָּ֥ה עִמָּדִ֑י

    שִׁבְטְךָ֥ וּ֝מִשְׁעַנְתֶּ֗ךָ

    הֵ֣מָּה יְנַֽחֲמֻֽנִי׃ (תהלים פרק כ”ג פסוק ד’ )