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When security updates are not installed, or installed slowly, end users are at an increased risk for harm. To improve security, software designers have endeavored to remove the user from the software update loop. However, user involvement in software updates remains necessary; not all updates are wanted, and required reboots can negatively impact users. We used a multi-method approach to collect interview, survey, and computer log data from 37 Windows 7 users. We compared what the users think is happening on their computers (interview and survey data), what users want to happen on their computer (interview and survey data), and what was actually going on (log data). We found that 28 out of our 37 participants had a misunderstanding about what was happening on their computer, and that over half of the participants could not execute their intentions for computer management.