President Barack Obama plans to use cutting-edge Internet tools to make the US government more responsive but he'll have to overcome creaky equipment, cumbersome regulations and potential embarrassment. Just ask Colleen Graffy, the Bush administration official whose Twitter posts about duty-free shopping and rented swimsuits during a State Department trip to Iceland drew widespread ridicule last month. “This is why diplomats stay off the record and boring,” Graffy said in a later Twitter post. Chatty diplomats will be only one of worries Obama's administration as it tries to drag the massive federal bureaucracy into the 21st century. Along with clunky computers and outdated rules, there is the obvious challenge of maintaining presidential dignity in the face of an often unruly online discourse. Obama's first week in the White House gave a taste of the difficulties to come. The administration unveiled a sleek new website the moment Obama became president, then failed to update it for days. Staffers settling in to the White House found their Web browsers filtered and their online chat software disabled. Even Obama himself battled to hold on to his beloved Blackberry e-mail device because of hacking concerns. On Monday, White House e-mail went down. David Almacy can understand. The former White House Internet director arrived in 2005 with a long list of upgrades for the Bush administration's staid online presence. “Everybody's looking at me and smirking,” Almacy said of his first meeting. “They said, ‘It would be great, but we can't do any of that.'” White House staff, accustomed during the campaign to using the latest communications tools to rally supporters, are likely to find their hands tied by the same regulations, experts say. Among them: u Administrators who delete inappropriate comments on government websites might run afoul of the First Amendment to the Constitution, which guarantees freedom of speech. u Federal contracting rules designed to ensure fairness could delay software upgrades and other improvements. u Online video could be hampered by a 1973 law that requires the government to provide real-time access, such as closed captioning, for disabled users. u A 2000 privacy rule that prohibits government websites from collecting and saving users' personal information limits their ability to customize content for individual visitors. u A 1978 law requires most White House communications to be archived, leading the Obama White House to block Instant Messaging rather than worry about any embarrassments that might come from online chats. u That law also requires Web pages to be archived every time they are changed. u Government websites must link to outside sites carefully, to prevent the appearance of an endorsement. u For these reasons, the White House may shy away from setting up a presence on popular outside sites like Facebook, which played a large role in the campaign.