Let me ask you something that seems simple, but really isn’t. Do you have an email address dedicated only to your sweepstakes hobby?

This is one of the very first things I teach people when they ask me how to get started with sweepstakes. And the reason I’m so firm about it is that I didn’t do it properly when I began. It took me years to realize how much it mattered.

When I started entering sweepstakes in 2001, I used my work email. Before you panic, I owned the business, but it was still not a great idea. Eventually, I opened a separate Yahoo email just for entering contests. What I didn’t expect was how long the transition would take. Some contests I had already entered didn’t end for months, so I had to keep using the old email until they wrapped up, while all new entries went to the new one. It took about six months for everything to fully shift over.

Fast forward to last year. As you know, I track my sweepstakes wins, and one of the biggest benefits of tracking is that patterns start to show up. When I looked at my spreadsheet for the year, something jumped out immediately: I hadn’t received a single large “you’ve won” email. I won 100 prizes, but the bigger wins came through Facebook notifications or PIN Code contests. Given the volume of PIN Code contests I entered, I found that a little suspicious.

Of course, the first thing people ask is, “Did you check your spam?” Yes. Every single day. These emails weren’t in spam. They weren’t anywhere.

That’s when a memory clicked.

A few months earlier, during one of my monthly Sweepstakes Master Classes, a seasoned sweeper mentioned he was on the longest dry spell of his life. Eight months with no wins. Several attendees and I grilled him. Where was he entering? How was he entering? What was his strategy? He was doing everything right. Then I asked one question that changed everything: What email address are you using? His answer: AOL.

I told him to switch to Gmail immediately. One week later, he emailed me. He’d already won three prizes. The emails weren’t going to spam. They were being blocked entirely at the server level. He never even had a chance to see them.

That memory, combined with my spreadsheet showing no large email wins, made me start paying closer attention.

Then something else happened.

I won a giveaway on Instagram during Sweepstakes Season: a romantic night out with dinner, a hotel stay, show tickets, and dessert. When the restaurant sent my reservation confirmation, I never received it. Not in spam. Not anywhere. I asked them to resend it to my Gmail work address instead, and it arrived instantly. The same thing happened with the hotel reservation.

At that point, it wasn’t a sweepstakes issue anymore. It was clearly an email issue.

Looking at my spreadsheet again, no big wins, missing emails, even remembering login codes not arriving, it all lined up. After 25 years, I realized it was time to make a change. In January, I opened a new Gmail address dedicated solely to sweepstakes entries.

As before, this isn’t an overnight switch. It took me six months the first time, and it will take time again. What’s interesting is that January, which is usually strong for me, was unusually quiet. That made me wonder how long my old email had been blocking messages and whether I missed wins simply because I wasn’t tracking carefully enough in 2024 to notice the pattern sooner.

That’s why tracking and email setup go hand in hand. One shows you what is happening. The other can quietly determine whether you even notice your wins.

If you’ve been on a dry spell, missing confirmations, or just have a gut feeling something’s off, listen to it and set up a new email address.

Because sometimes winning more isn’t about entering more. it’s about making sure your wins can actually reach you.