OK, I *did* spend a little more time on this and am now able to reproduce the behavior solely running the following Tcl code with tclsh: 

package require Tk
set w .text
catch {destroy $w}
toplevel $w
text $w.text -setgrid 1 -height 30 -font "Courier 20"
pack $w.text -expand yes -fill both
$w.text tag configure color1 -foreground red
$w.text insert 0.0 ">>>"
$w.text insert end "from" color1
$w.text mark set insert 0.0

Using Cocoa Tk 8.5.13, clicking on the "r" causes the insertion point to move to after the "r" and a second click moves the insertion point to before the "r".  Using the Apple-supplied Carbon Tk 8.4, the insertion point stays after the "r" on the second click.  I suspect the color tag has something to do with it.  I suggest if you want to pursue the issue, you should ask on one of the Tcl mailing lists, like the Mac-specific one (archived here http://dir.gmane.org/gmane.comp.lang.tcl.mac) or open an issue on the Tk tracker:
http://sourceforge.net/tracker/?group_id=12997&atid=112997