Error 258 means that the debugger failed to the connect to the target CPU. This can be for different reasons.
When troubleshooting the initial debug connection to the target CPU, it is recommended to use the CPU Reset debug command instead of Download debug command.
Check connection either through use of proper BlueBox debug adapter (iC5000, iC5700) or Active Probe. Double check that the pinout of the target debug connector matches with the one from the Debug Adapter or Active Probe.
In case of the Infineon DAP/DAPE Active Probe, providing two, DAP and DAPE connector, check also that the target Debug connector with the designation DAP is connected to the Active Probe DAP connector on the Active Probe and not accidentally to the Active Probe DAPE connector. If the embedded target features also "secondary" DAPE debug connector, double check that it's connected to the Active Probe DAPE connector and not DAP connector.
2. Necessary voltage is not connected to the target LPD debug connector or JTAG/Nexus debug connector.
Try to confirm this with another working BlueBox system. In case you confirm that the BlueBox hardware is damaged, contact iSYSTEM support.
If pins in DTM modules (in most cases pin 40 on ST1 connector) are bent, possible errors are: Error 250: FP5 Serial Communication error (Renesas RH850), DAP initialization failed (Infineon TriCore), CPU initialization failed (NXP/ST Power Architecture).
Try to test the BlueBox on another target or try to replace the CPU with a new one.
Disable all reset sources during debugging. See further explanation...
Open Hardware menu / CPU Options / JTAG and configure the Scan speed.
If JTAG debug protocol is selected, the JTAG scan speed is set in the JTAG tab, which is visible only when the JTAG debug protocol is selected and confirmed.
Refer to ARM Cortex-M: Error 258: Failed to initialize debug session for more information.
Refer to Infineon TriCore: Error 258: Failed to initialize debug session / DAP Initialization failed for more information.
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