I recommend you starting at 333x9, thats 3Ghz if I am correct. Leave your Vcore at 1.25 as this board tends to have horrible Vdroop.
Start by raising the FSB, this board tends to hate when you change the multiplier. My Q9550 never boots when I set the multiplier lower than 8.5
Make sure to Disable CPU Spread Spectrum
I got this from a thread, similar motherboard, E8500
I changed the settings in order to achieve 4Ghz on your E8400.
Multiplier should be at 9 for you.
Hope that helps
AI Overclock Tuner [Manual]
CPU Ration Setting [Auto]
FSB Frequency [445]
PCIE Frequency [100]
FSB Strap to North Bridge [400]
DRAM Frequency [Auto]
DRAM Timing [Auto]
DRAM Static Read Control [Auto]
DRAM Read Training [Auto]
MEM. OC CHarger [Auto]
AI Clock Twister [Auto]
AI Transaction Booster [Auto]
CPU Voltage [1.38125]
CPU GTL Voltage Reference(0/2) [Auto]
CPU GTL Voltage Reference(1/3) [Auto]
CPU PLL Voltage [Auto]
FSB Termination Voltage [Auto]
DRAM Voltage [1.8]
NB Voltage [Auto]
NB GTL Reference [Auto]
SB Voltage [Auto]
PCIE SATA Voltage [Auto]
Load Line Calibration [Auto]
CPU Spread Spectrum [Disable]
PCIE Spread Spectrum [Disable]
CPU Ratio Setting [Auto]
C1E Support [Disabled]
Max CPUID Value Limit [Disabled]
Intel (R) Virtualization Tech [Disabled]
CPU TM Function [Enabled]
Execute Disable Bit [Enabled]
Intel (R) SpeedStep (TM) Tech [Disabled]
Intel (R) C-STATE Tech [Disabled]
Start by raising the FSB, this board tends to hate when you change the multiplier. My Q9550 never boots when I set the multiplier lower than 8.5
Make sure to Disable CPU Spread Spectrum
I got this from a thread, similar motherboard, E8500
I changed the settings in order to achieve 4Ghz on your E8400.
Multiplier should be at 9 for you.
Hope that helps

AI Overclock Tuner [Manual]
CPU Ration Setting [Auto]
FSB Frequency [445]
PCIE Frequency [100]
FSB Strap to North Bridge [400]
DRAM Frequency [Auto]
DRAM Timing [Auto]
DRAM Static Read Control [Auto]
DRAM Read Training [Auto]
MEM. OC CHarger [Auto]
AI Clock Twister [Auto]
AI Transaction Booster [Auto]
CPU Voltage [1.38125]
CPU GTL Voltage Reference(0/2) [Auto]
CPU GTL Voltage Reference(1/3) [Auto]
CPU PLL Voltage [Auto]
FSB Termination Voltage [Auto]
DRAM Voltage [1.8]
NB Voltage [Auto]
NB GTL Reference [Auto]
SB Voltage [Auto]
PCIE SATA Voltage [Auto]
Load Line Calibration [Auto]
CPU Spread Spectrum [Disable]
PCIE Spread Spectrum [Disable]
CPU Ratio Setting [Auto]
C1E Support [Disabled]
Max CPUID Value Limit [Disabled]
Intel (R) Virtualization Tech [Disabled]
CPU TM Function [Enabled]
Execute Disable Bit [Enabled]
Intel (R) SpeedStep (TM) Tech [Disabled]
Intel (R) C-STATE Tech [Disabled]