Several studies suggest that deep convection that penetrates the tropical tropopause layer may influence the long-term trends in lower stratospheric water vapor. This thesis investigates the relationship between penetrating deep convection and lower stratospheric water vapor variability using historical infrared (IR) observations. However, since infrared observations do not directly resolve cloud vertical structure and cloud top height, and there has been some debate on their usefulness to characterize penetrating deep convective clouds, CloudSat/Calipso and Aqua MODIS observations are first combined to understand how to best interpret IR observations of penetrating tops. The major findings of the combined CloudSat/Calipso and Aqua MODIS analysis show that penetrating deep convection predominantly occur in the western tropical Pacific Ocean. This finding is consistent with IR studies but is in contrast to previous radar studies where penetrating deep convective clouds predominantly occur over land regions such as equatorial Africa. Estimates on the areal extent of penetrating deep convection show that when using IR observations with a horizontal resolution of 10 km, about two thirds of the events are large enough to be detected. Evaluation of two different IR detection schemes, which includes cold cloud features/pixels and positive brightness temperature differences (+BTD), show that neither schemes completely separate between penetrating deep convection and other types of high clouds. However, the predominant fraction of +BTD distributions and cold cloud features/pixels ≤ 210 K is due to the coldest and highest penetrating tops as inferred from collocated IR and radar/lidar observations. This result is in contrast to previous studies that suggest the majority of cold cloud features/pixels ≤ 210 K are cirrus/anvil cloud fractions that coexist with deep convective clouds. Observations also show that a sufficient fraction of penetrating deep convective cloud tops occur in the extratropics. This provides evidence that penetrating deep convection should be documented as a pathway of stratospheric-tropospheric exchange within the extratropical region. Since the cold cloud feature/pixel ≤ 210 K approach was found to be a sufficient method to detect penetrating deep convection it was used to develop a climatology of the coldest penetrating deep convective clouds from GridSat observations covering years 1998-2008. The highest frequencies of the coldest penetrating deep convective clouds consistently occur in the western-central Pacific and Indian Ocean. Monthly frequency anomalies in penetrating deep convection were evaluated against monthly anomalies in lower stratospheric water vapor at 82 mb and show higher correlations for the western-central Pacific regions in comparison to the tropics. At a lag of 3 months, the combined western-central Pacific had a small but significant anticorrelation, where the largest amount of variance explained by the combined western-central Pacific region was 8.25%. In conjunction with anomalies in the 82 mb water vapor mixing ratios, decreasing trends for the 1998-2008 period were also observed for tropics, the western Pacific and Indian Ocean. Although none of these trends were significant at the 95% confidence level, decreases in the frequency of penetrating deep convection over the 1998-2008 shows evidence that could explain in part some of the 82 mb lower stratospheric water vapor variability.