The Oregon Supreme Court opinion in State v. Speedis eviscerated the primary legal challenge to the upward departure factor of "on supervision at the time of the offense." (But it's worth noting that some challenges to here .)
Still, this is one aggravating factor that shouldn't worry you. The threat of it really shouldn't be a reason to fold your cards and go home, especially if you've got a triable case.
Why? Because if you do court-appointed work, almost of your felony clients are on supervision when they commit a new crime. And that's the key to keeping your client from being upward departed.
As I've noted in my dwindling list of viable challenges to upward departure factors, the most important challenge isn't in dispute. Even assuming the state can prove that your client is on supervision, ORS 138.222(3)(b) requires the trial judge to give reasons for upward departure that are substantial and compelling. State v. Wilson, 111 Or. App. 147, 826 P2d 1010 (1992) ("Under ORS 138.222(3)(b), we review whether the reasons given by the court are appropriate. That review is limited to whether the reasons are substantial and compelling.")
The Wilson Court explained that it would review the trial court's "explanation of why the circumstances are so exceptional that imposition of the presumptive sentence would not accomplish the purposes of the guidelines." [Emphasis added.]
Question: how is being "on supervision" an exceptional fact that merits an upward departure? When was the last time that someone who was, for example, a repeat property offender wasn't on supervision at the time of the newest crime? If 75% of REPO defendants were on supervision, that's not exceptional.
And the burden is on the state - and the judge - to show that the circumstances are - not just exceptional - so exceptional.
And I think it's worth noting that the legislature made "on supervision" a reason to deny optional probation in some cases, but it didn't enumerate "on supervision" as a reason to upward depart. Okay, fine, the legal challenge to that particularly non-enumerated factor no longer exists, but the common sense rule would still work with most judges. Yes, the defendant has done this before, and not that long ago. But that's why he/she is going to prison. And it's not like the typical probation includes any meaningful supervision anymore. You can't betray the hard work of a probation officer you've never met.