No purchase necessary to enter or win. A purchase does not improve your chances of winning. Void where prohibited by law.
Each drawing tier is independent. Entering one drawing does not enter you in any other drawing. You must enter each drawing you wish to participate in separately, each cycle.
City Insider Network operates three independent concurrent drawing tiers. Each tier has its own entry window, its own prize, its own sponsor, and its own eligibility requirements.
| Tier | Frequency | Eligibility |
|---|---|---|
| City Monthly Drawing | Monthly | Subscribers in that specific city who manually enter that month's window |
| Network Quarterly Drawing | Quarterly | All subscribers across all active cities in a state who manually enter that quarter's window |
| Annual Grand Drawing | Annually | All subscribers across all active cities and all states who manually enter that year's window |
Not all tiers may be active at all times. The current active drawings and their prizes are displayed at cityinsidernetwork.com/win.
Open to legal residents of the United States who are 18 years of age or older at the time of entry. Employees, contractors, and immediate family members of City Insider Network are not eligible. Void where prohibited by law.
There are no restrictions on repeat winners. Any eligible person may enter and win as many times as they qualify across any tier and any drawing period.
Important: Subscribers are not automatically entered in any drawing. Each subscriber must manually enter each drawing tier they wish to participate in, each cycle. Entering one drawing does not enter you in any other drawing.
Method 1 — Newsletter entry link (subscribers only): Each City Insider Network newsletter contains a unique entry link for every drawing tier that is currently open. Click the link in your newsletter to log your entry instantly. No form required. Your identity is verified by the link itself.
Method 2 — Win page entry form: Visit cityinsidernetwork.com/win, enter your email address, select the drawing you want to enter, and submit the form. If you are already a subscriber your entry is logged immediately. If you are not yet a subscriber you will be subscribed to the newsletter as part of the entry process.
Method 3 — Alternative means of entry (no subscription required): Send an email to hello@cityinsidernetwork.com with your first name and city in the subject line. One alternative entry per person per drawing window. This method requires no purchase or subscription. Your entry will be logged manually within 2 business days of receipt.
One entry per person per drawing tier per entry window. Duplicate entries for the same window are discarded. Entering one tier does not enter you in any other tier.
Each drawing tier uses a 30-day entry window per cycle. Windows open at 12:01 AM Eastern and close at 11:59 PM Eastern on the scheduled close date. Entry links are only active during an open window. Entries submitted after the close of a window are not eligible for that drawing.
City monthly drawing windows open on a recurring monthly schedule. Network quarterly and annual grand drawing windows are scheduled by City Insider Network administration and may not be active at all times. Current window status is shown at cityinsidernetwork.com/win.
One winner is selected per drawing tier per window using an automated cryptographically secure random selection system. Odds of winning depend on the total number of eligible entries received for that tier and window.
Winners are announced publicly on the City Insider Network YouTube channel as a live community event. The automated selection occurs at window close. The live broadcast is the public reveal of that selection.
The selected winner is notified by email within 24 hours of the drawing. The winner must respond within 48 hours of notification or a new winner will be selected.
Winners must complete all three steps before receiving payment: (1) submit a winner story, (2) submit a completed W-9 tax form, and (3) receive prize payment. Steps must be completed in order.
Step 1 — Winner story: Within 7 days of winner notification, the winner must complete a winner story submission at cityinsidernetwork.com/winner. The winner answers five short questions about their winning experience. City Insider Network writes the community story from those answers. The winner reviews and approves the story before publication. A photo is required. Failure to submit within 7 days results in forfeiture and selection of a new winner.
Step 2 — W-9 tax form: After the winner story is submitted, City Insider Network will email the winner a W-9 form (IRS Form W-9, Request for Taxpayer Identification Number). The winner must complete and return the signed W-9 before payment is released. The W-9 is collected and stored off-platform. No SSN or Tax ID is ever entered on any City Insider Network website or form.
Step 3 — Payment: Payment is released within 7 days of receiving both the approved winner story and the signed W-9. Payment is delivered via Cash App, Venmo, Zelle, or check at City Insider Network's discretion. Payment is made from a designated prize-reserve account separate from operating funds.
All prizes are taxable income. Winners are solely responsible for all federal, state, and local tax obligations arising from receipt of any prize.
City Insider Network will issue IRS Form 1099-MISC to any winner whose cumulative annual winnings across all City Insider Network drawing tiers and all cities exceed $600 in a calendar year. Cumulative winnings are tracked across all tiers and all cities. Winners are responsible for reporting all prize income regardless of whether a 1099-MISC is issued.
City Insider Network is not responsible for any tax liability incurred by winners. Winners should consult a qualified tax professional regarding their obligations.
Prize amounts are set by City Insider Network administration and may vary by city, tier, and drawing period. Current prize amounts for all active drawings are displayed at cityinsidernetwork.com/win. Prize amounts are not guaranteed to remain the same across drawing cycles and may be adjusted with notice.
Prizes have no cash value except where the prize is itself a cash or cash-equivalent payment. Prizes may not be transferred, substituted, or exchanged except at City Insider Network's sole discretion.
By entering, entrants grant City Insider Network a non-exclusive, royalty-free license to use their first name, city, and any winner story content they submit for publication in the newsletter, on the website, and on City Insider Network social media channels. Full last names, email addresses, and personal contact information are never published. This grant is a condition of entry and applies to all entrants.
Winner stories, photos, and first names are published after story approval as proof that drawings are conducted fairly and prizes are delivered.
Each drawing tier may have an exclusive sponsor for a given period. Sponsors are identified in the newsletter, on the drawing page, and during the live drawing broadcast. Sponsor slots do not affect winner selection or entry eligibility.
Right of rescission: Drawing sponsorship payments are non-refundable after the 3-day right of rescission period from the date of payment. Sponsors who cancel within 3 days of payment receive a full refund. After day 3, no refunds are issued regardless of remaining term.
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