2019 AMC 10B Problem 12

What is the greatest possible sum of the digits in the base-seven representation of a positive integer less than $2019$ ?

$\textbf{(A) } 11 \qquad\textbf{(B) } 14 \qquad\textbf{(C) } 22 \qquad\textbf{(D) } 23 \qquad\textbf{(E) } 27$

Full credit goes to MAA for authoring these problems. These problems were taken on the AOPS website.