TimeMachine worked, now fails

My Imac is connected to an external hard drive. I am only using 192.6 GB of my 500 GB internal hard drive. My external hard drive is also 500 GB. But when I go to back up, I get a message telling me that there are only 147.5 GB available on the external hard drive (because 279.36 are in use) and it needs more to back up. If TM backs up incrementally and deletes the earliest backups as the drive fills up theoretically this cannot be happening. So why is it? I only use this drive for TM backups. I want to back up my entire system as I have been used to in the past and not exclude files.

Here's a copy of my last Console session, showing Time Machine deleting backups...
+May 12 20:46:17 BigMacintosh-2 /System/Library/CoreServices/backupd[147]: No pre-backup thinning needed: 2.37 GB requested (including padding), 236.91 GB available+
+May 12 20:48:07 BigMacintosh-2 /System/Library/CoreServices/backupd[147]: Copied 1865 files (1.9 GB) from volume Macintosh HD.+
+May 12 20:48:09 BigMacintosh-2 /System/Library/CoreServices/backupd[147]: No pre-backup thinning needed: 100.0 MB requested (including padding), 234.99 GB available+
+May 12 20:48:20 BigMacintosh-2 /System/Library/CoreServices/backupd[147]: Copied 907 files (8 KB) from volume Macintosh HD.+
+May 12 20:48:25 BigMacintosh-2 /System/Library/CoreServices/backupd[147]: Starting post-backup thinning+
+May 12 20:48:27 BigMacintosh-2 /System/Library/CoreServices/backupd[147]: Deleted backup /Volumes/Big TimeMachine/Backups.backupdb/Bob's Big Mac/2008-05-11-202341: 234.99 GB now available+
+May 12 20:48:32 BigMacintosh-2 /System/Library/CoreServices/backupd[147]: Deleted backup /Volumes/Big TimeMachine/Backups.backupdb/Bob's Big Mac/2008-05-11-192455: 236.87 GB now available+
+May 12 20:48:35 BigMacintosh-2 /System/Library/CoreServices/backupd[147]: Deleted backup /Volumes/Big TimeMachine/Backups.backupdb/Bob's Big Mac/2008-05-11-182346: 236.88 GB now available+
+May 12 20:48:41 BigMacintosh-2 /System/Library/CoreServices/backupd[147]: Deleted backup /Volumes/Big TimeMachine/Backups.backupdb/Bob's Big Mac/2008-05-11-172506: 238.77 GB now available+
+May 12 20:48:47 BigMacintosh-2 /System/Library/CoreServices/backupd[147]: Deleted backup /Volumes/Big TimeMachine/Backups.backupdb/Bob's Big Mac/2008-05-11-162527: 240.70 GB now available+
+May 12 20:48:47 BigMacintosh-2 /System/Library/CoreServices/backupd[147]: Post-back up thinning complete: 5 expired backups removed+
+May 12 20:48:47 BigMacintosh-2 /System/Library/CoreServices/backupd[147]: Backup completed successfully.+
I presume it checked to see if it had redundant backups, and then deleted them...I don't know for sure, in this case,
Bob

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I can see you are having some issues with scan to folder/email, I would like to see if I can help you on this issue.
First, let me ask you, what is the operative system of the computer that you shared the folder for scan to folder?
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