The seal has the elements of the city flag adopted in January 1965, but some details have changed over the years.The left rendering approximates the original seal, and the right rendering is based on a physical flag obtained from the the city government in early June 2020 (age unknown).

Sourcing related to this image (seals):

EARLY SEAL:

• https://web.archive.org/web/20200416202254/https://msa.maryland.gov/msa/mdmanual/37mun/annapolis/html/a.html

EARLY SEAL:

• https://web.archive.org/web/20200310185543/https://www.annapolis.gov/CivicSend/ViewMessage/message/75797

• ...and included in emails from Annapolis government in 2020

FLAG with ROUND-TOP CROWN

• https://web.archive.org/web/20200605044136/https://www.crwflags.com/fotw/images/u/us-md-an-l.gif

Sourcing related to flag:

— Suggested caption for the flag image:

Annapolis's first official flag, adopted in January 1965, is styled after the personal royal badge of Queen Anne after whom the city was named. Resembling the floral badge of Great Britain, a crown hovers over a thistle (representing Scotland) and a rose (representing England), growing from a single stalk to portray their union. The motto Vixi liber et moriar means "I have lived free and will die so".

— Source for suggested caption:

(January 12, 1965). "DAR Chapter Presents City With Official Banner". Evening Capital (Vol. LXXXI, No. 9): 1. Image caption: "City's First Flag".

— Quotation from the Annapolis Evening Capital, January 12, 1965:

Image caption on page 1 of newspaper: "City's First Flag ... The emblem which the flag depicts was the personal badge of Queen Anne of England, for whom Annapolis was named, which she wore to symbolize the union between England--represented by the rose on the right--and Scotland--represented by the thistle on the left. The red rose is of the House of Lancaster and the white rose of the House of York. The hovering crown further emphasizes unity. At the flag's base is the motto, "Vixi liber et moriar" ("I have lived free and will die so").