Forecasters at the Storm Prediction Center were faced with many challenges during the 3 May 1999 tornado outbreak. Operational numerical forecast models valid during the outbreak gave inaccurate, inconsistent and/or ambiguous guidance to forecasters, most notably with varying convective precipitation forecasts and underforecast wind speeds in the middle and upper troposphere, which led forecasters (in the early convective outlooks) to expect a substantially reduced tornado threat compared to what was observed. That, combined with relatively weak forecast and observed low-level convergence along a dryline, contributed to much uncertainty regarding timing and location of convective initiation. Consequently, as the event approached, observational diagnosis and analysis became more important, and were critical in identification of the evolution of the outbreak. Ultimately, tornadic supercells developed earlier, were more numerous, and produced more significant tornadoes than anticipated. While forecasters dealt with the meteorological facets of the tornadic storms the evening of 3 May 1999, there were other areas of simultaneous severe storm development, and one of the tornadoes posed a threat to the facility and family members of the forecast staff. These uncertainties and challenges are discussed in the context of SPC convective outlooks and watches for this outbreak. Recommendations are made for continued research aimed at improving forecasts of convective initiation and mode.