Information Technology Investment Oversight Enhancement and Waste Prevention Act of 2008

Information Technology Investment Oversight Enhancement and Waste Prevention Act of 2008 - Expands the requirement that each head of an executive agency identify, in strategic information resources management plans, any major information technology acquisition program, or any phase or increment of such program, that has significantly deviated from the cost, performance, or schedule goals established for the program. Defines "significantly deviated" as earned value management variance that is at least 20% from the original baseline established at the commencement of an information technology acquisition program.

Requires each Chief Information Officer of a federal agency to: (1) identify its major IT investments that are most critical; and (2) designate those most mission critical IT investment projects as core IT investment projects or core projects after considering specified factors. Defines "IT investment project" as an information technology system or acquisition that: (1) requires special management attention due to its importance to the mission or function of its agency; (2) is for financial management and obligates more than $500 million annually; (3) has significant program or policy implications; (4) has high executive visibility; (5) has high development, operating, or maintenance costs; (6) is funded through other than direct appropriations; or (7) is defined as major by the agency's capital planning and investment control process.

Requires the project manager for an IT investment project to submit a report to the Chief Information Officer not later than 14 days after the end of each fiscal quarter (or upon making a determination that a project has significantly or grossly deviated since the issuance of any quarterly report) that includes: (1) a description of the cost, schedule, and performance of such projects; (2) the original and current project cost, schedule, and performance benchmarks; (3) the quarterly and cumulative cost, schedule, and performance variance related to each project; (4) any known, expected or anticipated changes to project schedule milestones or project performance benchmarks; (5) the current cost, schedule, and performance status of all projects previously identified as significantly deviated or grossly deviated (i.e., more than 40% variance from the original baseline); and (6) any corrective actions taken.

Requires the Chief Information Officer, upon receiving such a report, to: (1) determine if any project has significantly or grossly deviated and report such determination to the agency head; (2) report any such significant or gross deviations to appropriate congressional committees, the Director of the Office of Management and Budget (OMB), and the Government Accountability Office (GAO); (3) develop and implement a remedial action plan to address gross deviations; and (4) establish a program to improve the information technology processes overseen by the Chief Information Officer.

Requires the Administrator of the Office of Electronic Government and Information and Technology at OMB (the E-Gov Administrator) to establish an IT Strike Force to assist agencies in avoiding significant and gross deviations in the cost, schedule, and performance of IT investment projects and take specified actions to avoid or reduce such deviations.

Requires the OMB Director to include in the annual report to Congress on the Benefits of E-Government Initiatives a summary of the composition and activities of the IT Strike Force and its effectiveness.