Are you holding the button all the time while you are plugging it into the USB Port? Is the Blue LED blinking quickly? When you open the bootloader host do you see the device in the window of the bootloader host? As you have two devices it seems strange that both of the devices have and issue but they could. see this Using the CY8CKIT-049 to Program Another PSoC® 4 - KBA93541 | Cypress Semiconductor
The USB-Serial device acts as a USB-UART bridge for the CY8CKIT-049-4xxx development kit. Have you tried to change the default settings?
Do you want to use any other configuration controls such as GPIO, SPI, and I2C that use the Cypress vendor driver on the PC? If yes, please make use of section: 'Additional Features of the USB-Serial Device' of http://www.cypress.com/file/141306/download
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So it turns out this was due to an enumeration problem.
In device manager I had to show hidden devices and manually uninstall AND DELETE (This is crucial unless you want to reboot your machine every 5 bootloads or so) the drivers corresponding to all of the 'ghost' COM port devices, as well as the 'usb-serial vendor MFG' devices which appear under universal serial bus controllers.
At this point PSOC will once again recognise the device. Sometimes you may have to do this repeatedly, but for some reason I haven't had to do this for a few days (not complaining).
Also take note that if you, like myself, are toying with other USB programmable devices such as arduino Bootloader host likes to toy with your baud rate for no apparent reason sometime and set it to 9600!