MacOS – “Not enough space” on partitioning

My suggestion

Don't try to resize from the Recovery partition. Boot into the normal partition and resize from there.

Background

diskutil list is misleading you. It is not the position of the recovery partition which is your problem.

I had a very similar setup, and here is the output of diskutil list for me:

  #:                       TYPE NAME                    SIZE       IDENTIFIER
   0:      GUID_partition_scheme                        *500.1 GB   disk0
   1:                        EFI                         209.7 MB   disk0s1
   2:                  Apple_HFS Macintosh HD            423.6 GB   disk0s2
   3:                 Apple_Boot Recovery HD             650.0 MB   disk0s3
   4:                  Apple_HFS Temp Partition Test ... 74.8 GB    disk0s4
   5:                 Apple_Boot Recovery HD             792.2 MB   disk0s5

Partitions 4 and 5 had a dev version of Lion on them. I have just used Disk utility to delete partitions 4 and 5 and resize partition 2 to fill the space.

This worked - Disk Utility resized the main drive with no problem. So what have I done which is different to you? Well, I resized the main partition from booting into the main partition not the Recovery Partiion. You can resize a partition that you have booted from in Disk Utility.

It makes sense that the recovery partition would "get in the way" if you have booted from it, so I suspect that above suggestion might work for you.

Lion has a hidden partition which contains recovery information. Shrinking the partition, according to an Apple employee, is not supported. He hooked up my MBP to an external hard drive and wiped and reinstalled Lion in order to fix things.

In more detail, what happens is this: When you try and resize the main partition, it doesn't include the recovery partition. When you hit "Apply Changes," it does a checksum to make sure that nothing's accessing the drive. It then gets started, doing another checksum, and discovers that something's changed, breaking the previous checksum.