The Center for Democracy and Technology has put together a handy online guide for anyone involved in electoral politics online called, appropriately, the NetDemocracy Guide. It's an outgrowth of the fight between political bloggers and the Federal Election Commission, which began when the FEC hinted at drastic new regulations that would have unnecessarily curtailed much web-based political speech a little over a year ago, and culminated earlier this year with the agency essentially deciding to leave most unpaid and low-cost online politicking untouched.
The guide does a solid job of explaining the differences between "uncompensated internet activity" that is specifically exempt from regulation, and the kinds of "public communication" that can trigger reporting requirements and conceivably may also count as contributions to campaigns.
The CDT report is not meant to serve as formal legal advice. But, in general, it makes clear that if all you're doing online is commenting on blogs, posting in support of candidates on your own blog or on other sites, sending emails to friends about candidates you support, creating a website or even making a video supporting or opposing a candidate and posting it on a video-sharing site, you have nothing to worry about.
CDT is careful not to make blanket statements about what lines you have to be careful about, and I think some users may be a bit frustrated to not find a simple checklist to help them determine if any of their activities cross those lines. But there's a feedback form included, and perhaps the center will create such a checklist as the site matures.
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