Timeline subject to tweaking. Major changes will be announced.
DURING CONTEST:
Friday, June 14th: 8pm PST (11pm Eastern Time): I create the contest group and the contest goes live. Only stories published after this point in time qualify for the contest.

Rest of night: I manage questions and comments regarding the contest

Friday, June 21st: I send out an enncouraging message, announce any new judges or artists

Sunday, June 30th: Halfway through announcement

Thursday, July 4th: Independence Day in the United States, which has no bearing on this contest.

Sunday, July 7th: One week left announcement

Friday, July 12th, 12am: 72 hours to go!

Friday evening: I remind everyone that those who private message me begging for an extension and having an at least mediocre reason for it get one extra day to finish their stories up.

Saturday, July 13th, 12am: 48 hours to go!

Sunday, July 14th, 12am: 24 hours to go
12pm: 12 hours to go!
6pm: 6 hours to go! I again remind everyone that those who private message me begging for an extension and having an at least mediocre reason for it get one extra day to finish their stories up.
9pm: 3 hours to go!
11pm: 1 hour to go!
11:59:59pm: Contest ends!

AFTER CONTEST:
Monday, July 15th, 12am: When I say I'm gonna close contest submissions
1:30am: When I actually close contest submissions
Afternoon: Blog post reviewing how judging will work, how many entries we had, etc.
11:59:59pm: Deadline for late submissions with PM approval

Tuesday, July 16th, 12am: Contest folder closes, no ifs, ands, or buts

Mid-morning: First round of judging begins

Saturday, July 20th: First round of judging ends

Sunday, July 21st: Second round of judging begins

Thursday, July 25th: Second round of judging ends

Friday, July 26th: Finals judging begins

Tuesday, July 30th: Finals judging ends

RESULTS:
Saturday, August 3rd, sometime in the afternoon or evening: Winners announced live at BronyCon, with multiple livestreams available online

Later that day or possibly simultaneously: Winners published online

Rest of August: Winners coordinate with artists and audiobook readers and me for their prizes
Scores for all stories, without judges names, released to public, feedback possibly available upon request
I bask in the glory of having run the best FimFiction contest ever!

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No, this is an unofficial thing