                               In the

    United States Court of Appeals
                 For the Seventh Circuit
                     ____________________
No. 16-3583
UNITED STATES OF AMERICA,
                                                   Plaintiff-Appellee,

                                 v.

RICKY OLSON,
                                               Defendant-Appellant.
                     ____________________

         Appeal from the United States District Court for the
                   Western District of Wisconsin.
          No. 16-CR-001-BBC — Barbara B. Crabb, Judge.
                     ____________________

  ARGUED SEPTEMBER 27, 2017 — DECIDED JANUARY 25, 2018
                ____________________

   Before WOOD, Chief Judge, and FLAUM and KANNE, Circuit
Judges.
    WOOD, Chief Judge. We do not know whether Ricky Olson
entered a voluntary and intelligent guilty plea on
September 9, 2016, because the district court never asked the
right questions. Several weeks earlier, the court had granted
Olson’s motion to withdraw his guilty plea and to proceed to
trial. But matters did not rest there. Instead, on September 9
the district court brought the motion to withdraw the guilty
2                                                   No. 16-3583

plea back to life (that is, the one it had already disposed of),
and this time summarily denied it. The court ultimately
sentenced Olson to 180 months of incarceration and 20 years
of supervised release. On appeal, Olson complains that the
irregular proceedings surrounding his plea failed to comply
with the rules of criminal procedure. We agree with him.
Because the September 9 proceedings resulted in a new
change of plea, which the district court accepted without
conducting the colloquy required by Federal Rule of Criminal
Procedure 11, we reverse and remand.
                                I
    Olson was convicted on charges of distributing sexually
explicit photographs of his minor daughter in violation of
18 U.S.C. § 2252(a)(2). Our concern, however, is not with the
facts that lie behind his conviction, nor is it with any defense
he plausibly might raise. It is with the procedure the court fol-
lowed in obtaining the guilty plea on which it relied. Olson
argues that the court committed plain error by re-activating
Olson’s earlier guilty plea and then accepting that plea with-
out conducting a proper colloquy under Rule 11.
    Olson first pleaded guilty to violating section 2252(a)(2) on
April 6, 2016. As part of an accompanying plea agreement, he
stipulated to conduct charged in three other counts of his
indictment and waived the right “to appeal his conviction and
any sentence of imprisonment of 180 months or less.” In
exchange, the government promised to dismiss all charges
not covered by his guilty plea. Before accepting the plea on
April 6, the district court conducted a Rule 11 colloquy. Part
of Olson’s current appeal is an attack on that exchange as
inadequate and plainly erroneous. He directs our attention to
a confused discussion about whether the images were
No. 16-3583                                                    3

“sexually explicit” as required by section 2252(a)(2). Although
Olson eventually conceded that the photographs showed his
daughter naked, he repeatedly denied that they were sexually
explicit, showed his daughter’s vagina or depicted her
masturbating, and he stated that he “d[id]n’t understand” the
court’s questions. Despite this confusion, the court accepted
the plea.
    At an ex parte hearing on August 26, 2016, Olson moved to
withdraw his guilty plea, and his attorney, Peter Moyers,
moved to withdraw from representation. The district court
orally granted both motions and memorialized its ruling in
writing. Olson complained at the hearing that he had not un-
derstood the plea agreement, had pleaded under pressure
from his attorney, and had not thought that the images were
sexually explicit. Moreover, according to Olson, the theft of
his glasses while he was in prison had prevented him from
reading his plea agreement before signing it. As a result, he
asserted, the agreement had been “kind of paraphrased” for
him. Olson further maintained that he had not understood his
potential sentence and had not known he would qualify as a
sex offender. He displayed confusion over what crimes were
covered by his April 6 plea. At one point he even suggested
that he had pleaded guilty to four charges that the plea agree-
ment in fact required the government not to pursue. Olson
claimed that he had pleaded guilty despite his belief that the
photographs were not sexually explicit only after his attorney
had flatly instructed him to “[p]lead guilty. The DA is just mis-
taken, we’ll hash all that out later.” Olson complained that
Moyers refused to file objections to the presentence report,
warning Olson that, if Moyers did object, the judge would im-
pose a 30-year sentence on Olson. Moyers equated this term
to “a life sentence” or dying in prison. (We stress that none of
4                                                  No. 16-3583

these allegations about Moyers’s performance has been sub-
stantiated; we nonetheless present Olson’s subjective view be-
cause it informed the district court’s decision to grant his mo-
tion and informs our review of the intelligence and voluntar-
iness of his plea.)
    At Olson’s request, an additional plea-related hearing took
place on September 9. Joe Bugni, rather than Moyers, now
represented him. During a brief exchange, Olson stated that
he was “definitely guilty of one charge” and expressed a be-
lief that his “best course [was] just to throw [him]self at the
mercy of the court.” Without further ado, the district court
then announced it would move forward with sentencing. At
Bugni’s prompting, the court also purported to deny the al-
ready-granted August 26 motion to withdraw Olson’s guilty
plea and Moyers’s motion to withdraw from representation
(though Moyers never reappeared, and Bugni continued to
represent Olson). On that occasion, the court did not hold a
Rule 11 colloquy or anything resembling one.
    The district court sentenced Olson on September 26 and
entered final judgment that day. He now appeals both his
conviction and sentence. Olson argues that the district court
plainly erred by dispensing with a Rule 11 colloquy on
September 9, when he indicated his willingness to plead
guilty. In the alternative, he asks that we vacate his sentence
because of the court’s failure to calculate the guidelines range
and consider the factors in 18 U.S.C. § 3553(a) before imposing
a term of supervised release.
                               II
   Rule 11 of the Federal Rules of Criminal Procedure re-
quires a trial court to “address the defendant personally in
No. 16-3583                                                       5

open court” before accepting his guilty plea. FED. R.
CRIM. P. 11(b). During this colloquy, the court must convey
specific information about his rights and the consequences of
his plea, and it must satisfy itself that he understands those
rights. FED. R. CRIM. P. 11(b)(1). The court also must ensure
that the plea is voluntary, FED. R. CRIM. P. 11(b)(2), and that it
is supported by a factual basis, FED. R. CRIM. P. 11(b)(3). While
not itself of constitutional dimension, Rule 11 helps to ensure
compliance with the constitutional rule that a guilty plea must
be knowing and voluntary. McCarthy v. United States, 394 U.S.
459, 465, 467 (1969), superseded on other grounds by rule,
FED. R. CRIM. P. 11(h), as recognized in United States v. Cross,
57 F.3d 588, 591 (7th Cir. 1995); see also Boykin v. Alabama,
395 U.S. 238, 242–43 (1969). The rule also aids appellate re-
view by creating a contemporary record. McCarthy, 394 U.S.
at 465, 467. In order to plead intelligently in the constitutional
sense, a defendant “must understand not only the nature of
the charge … but also that his or her conduct actually falls
within the charge.” United States v. Frye, 738 F.2d 196, 199
(7th Cir. 1984).
    Because Olson raised no objection to the district court’s
method of proceeding, we review the court’s deviation from
the strictures of Rule 11(b) for plain error. United States v. Vonn,
535 U.S. 55, 58 (2002); see FED. R. CRIM. P. 11(h). Therefore,
Olson bears the burden of showing: (1) an error, (2) that is
plain or obvious, (3) that affects his “substantial rights,” and
(4) that “seriously affect[s] the fairness, integrity, or public
reputation of judicial proceedings.” Puckett v. United States,
556 U.S. 129, 135 (2009); United States v. Anderson, 604 F.3d 997,
1002 (7th Cir. 2010).
6                                                             No. 16-3583

                                     A
    As a preliminary matter, we reject the government’s view
that Olson entered a guilty plea only once, on April 6.
According to the government, rather than enter a new guilty
plea on September 9, Olson merely moved to withdraw his
August 26 motion to withdraw his April 6 guilty plea. Thus,
it reasons, on September 9 the district court simply restored
the status quo prior to August 26, i.e., the April 6 guilty plea.
Because Olson already had pleaded guilty on April 6 and
waived no additional rights on September 9, it continues, the
district court did not need to engage in a second, redundant
Rule 11 colloquy. See, e.g., United States v. Taylor, 984 F.2d 618,
619 (4th Cir. 1993) (holding no second Rule 11 colloquy
mandated when defendant “equivocates about his guilty plea
after the initial plea hearing”). The government further argues
that the district court conducted a proper Rule 11 colloquy
when Olson entered his guilty plea on April 6. Therefore, it
concludes, the district court committed no error—plain or
otherwise.
   The government’s argument fails for a simple reason: Un-
der the circumstances we have outlined, the district court
could not “reinstate” the April 6 plea. 1 When Olson filed the

    1 In other circumstances, some of our sister circuits have found a rein-

statement to be proper. Because those circumstances differ from those be-
fore us, we have no occasion to consider the soundness of those circuits'
approach. For instance, in United States v. Farrah, 715 F.2d 1097 (6th Cir.
1983), the defendant initially pleaded guilty pursuant to an oral plea
agreement. On the day of sentencing, however, it became clear that there
was uncertainty over the maximum possible period of imprisonment. This
prompted the district court to permit Farrah to withdraw his guilty plea.
Id. at 1097–98. Later, he pleaded guilty again, this time pursuant to a writ-
ten plea agreement that called for a maximum of one year in prison. The
No. 16-3583                                                                  7

September 9 motion, he did not argue that the district court
had granted the August 26 motion in error and that the
April 6 plea had been fine all along. Indeed, he is still raising
objections to the Rule 11 colloquy that accompanied the April
plea. That left the “not guilty” plea entered on August 26 as
the operative baseline. The September 9 motion thus had the
effect of changing Olson’s plea from “not guilty” to “guilty.”
In other words, the September 9 statement represented a new
guilty plea, to which Rule 11 applied independently. E.g., FED.
R. CRIM. P. 11(b)(1) (requiring colloquy “[b]efore the court ac-
cepts a plea of guilty” (emphasis added)). In this situation,
Rule 11’s requirements are mandatory and plain: “the court
must address the defendant,” “must inform” him of his rights
and ensure his understanding, and “must … determine that
the plea is voluntary.” FED. R. CRIM. P. 11(b)(1), (2) (emphasis
added). The district court obviously erred by conducting no



district court imposed a one-year sentence, whereupon Farrah moved
again to withdraw his plea, claiming that he believed that he would re-
ceive a four-month sentence. Again, the court allowed him to withdraw
his plea, but the government moved for reconsideration of the latter order.
Id. at 1098. The court granted the government’s motion, and the Sixth Cir-
cuit affirmed. Id. at 1098–99. In that setting, no one argued that a new
Rule 11 colloquy was required nor was there any reason for the court sua
sponte to consider the issue, given its finding that the defendant was fully
aware the second time around that he faced up to a year in prison. Unlike
in Olson’s case, the district court in Farrah had erred in granting the mo-
tion to withdraw in the first place and, by reinstating the guilty plea,
simply corrected its own mistake. Id. at 1099; see also United States v. Chant,
No. 98-10088, 1999 WL 1021460 (9th Cir. 1999) (unpublished disposition)
(affirming reinstatement of a guilty plea following motion for reconsider-
ation because a change in applicable law had rendered a prior order per-
mitting withdrawal erroneous).
8                                                    No. 16-3583

Rule 11 colloquy on September 9. This satisfies the first two
requirements of plain error review.
    The next question is whether the court’s failure to conduct
a Rule 11 colloquy on September 9 prejudiced Olson’s sub-
stantial rights. When weighing whether a “variance” from
Rule 11 affected substantial rights, see Rule 11(h), we consider
“whether under the totality of the circumstances, the plea was
voluntary and intelligent.” Cross, 57 F.3d at 591. To prevail, the
appellant “must show a reasonable probability that, but for
the error, he would not have entered the plea.” United States
v. Dominguez Benitez, 542 U.S. 74, 83 (2004). This test does not
demand incontrovertible proof: as we have explained, “[o]ne
step … along the way to the defendant’s demonstration that
the error affected his decision to plead guilty is to look at
whether the defendant understood his plea agreement.”
United States v. Sura, 511 F.3d 654, 662 (7th Cir. 2007).
    Citing United States v. Vonn, the government contends that
the April 6 colloquy serves as evidence that the omission of a
Rule 11 colloquy on September 9 was not prejudicial. The gov-
ernment is correct that we must examine the record as a whole
when reviewing a particular Rule 11 violation for plain error.
As Vonn observes, under some conditions “defendants may be
presumed to recall information provided to them prior to the
plea proceeding.” 535 U.S. at 75. The question is whether that
presumption applies here.
   In answering this question, we will assume that Vonn
applies to the kind of complete omission of a Rule 11 colloquy
that occurred on September 9. Yet, Vonn directs us to consider
the entire record, which includes not only the September 9
proceedings, but also the April 6 colloquy (itself arguably
insufficient in light of Olson’s professed confusion about the
No. 16-3583                                                  9

content of the photographs) and the August 26 hearing. Taken
as a whole, this record leaves us with serious concern about
the intelligence and voluntariness of Olson’s September 9
statements. On August 26, Olson told the court that he had
not understood the written plea agreement or the potential
sentence, and that he had not believed himself guilty of
distributing “sexually explicit” content. While some of his
more cogent objections might have indicated an improved
understanding of the consequences of pleading guilty, other
statements revealed continued confusion and raised
voluntariness concerns. For example, while the court
permitted Moyers to withdraw as Olson’s attorney, Olson told
the court on August 26 that he acted on the advice of prisoners
and guards; on September 9 he cited the guidance of fellow
inmates. Likewise, while Olson did state that he was
“definitely guilty of one charge” on September 9, he never
specified which one. Confronted with this vague statement,
we recall Olson’s apparent incorrect belief on August 26 that
he previously had pleaded guilty to multiple counts and his
repeated denial that the images violated section 2252(a)(2).
These circumstances give us no confidence that Olson
understood what would follow from his guilty plea of
September 9.
    And these are not the only signs of a process gone awry.
When we review the record, further ambiguities appear. Why
did Olson plead guilty on September 9? What did he expect
to obtain in return, if anything? Did Olson enter a naked plea,
unaccompanied by any agreement, or was the April 6 plea
agreement still in force despite the August 26 order? Olson’s
own statement that he wished “just to throw [him]self at the
mercy of the court” would suggest the former possibility; yet,
10                                                    No. 16-3583

he, the prosecution, and the district court all seem to have as-
sumed that the plea agreement remained in effect. If he acted
on this latter assumption, it was unsupported and inadequate
to support his plea.
    This court has consistently held that a defendant’s sub-
stantial breach of a plea agreement permits the government
to rescind the deal. E.g., United States v. Kelly, 337 F.3d 897, 901
(7th Cir. 2003). We have identified a variety of substantial
breaches: for example, absconding before sentencing, United
States v. Munoz, 718 F.3d 726, 729–30 (7th Cir. 2013), refusing
to testify against a co-defendant as promised, United States v.
Ataya, 864 F.2d 1324, 1338 (7th Cir. 1988), and failing to com-
ply with an obligation to cooperate with an investigation,
Kelly, 337 F.3d at 901–02. Olson’s decision not to plead guilty,
had it stuck, would similarly have robbed the government of
the benefit of its bargain and forced it to invest substantial re-
sources in trial preparation. In fact, Olson’s August 26 deci-
sion to withdraw his guilty plea undermined the agreement’s
raison d’être. Therefore, it presumably freed the government
to pursue all counts in the indictment. All of this is to say that,
as of September 9, Olson might have had no idea of the con-
sequences of his new guilty plea, and thus might not have en-
tered his plea intelligently. When we as judges cannot deter-
mine the legal consequences of Olson’s plea, we decline to
conclude that he could.
    The final aspect of our plain error analysis looks to the
“fairness, integrity, or public reputation of the judicial pro-
ceedings.” Anderson, 604 F.3d at 1002. Safeguarding these val-
ues may require that we reverse a conviction “independent of
the defendant’s innocence.” United States v. Olano, 507 U.S.
725, 736–37 (1993). Our reasoning in United States v. Sura
No. 16-3583                                                     11

strongly supports reversing the conviction in Olson’s case. In
Sura, we held that omitting from a Rule 11 colloquy any dis-
cussion of a defendant’s waiver of appellate rights in a plea
agreement seriously offended judicial values and was enough
to set aside the entire, otherwise knowing, plea agreement.
511 F.3d at 663. Olson’s potential failure to comprehend the
nature of his offense, whether he had committed it, and
whether a plea agreement remained effective each justifies
setting aside his plea. These are essential aspects of any guilty
plea—even more important than the subsidiary condition of
the bargain at issue in Sura. Were we to affirm Olson’s convic-
tion and imprisonment under these circumstances, we would
undermine confidence in the integrity of the judicial process.
                                B
    Just as we find that Olson did not waive his right to a trial,
we hold that he did not waive his right to appeal his convic-
tion. The government first argues that Olson waived this right
through an express term in the April 6 plea agreement. Yet an
invalid waiver cannot insulate an invalid plea:
   Waivers of appeal must stand or fall with the agree-
   ments of which they are a part. If the agreement is vol-
   untary, and taken in compliance with Rule 11, then the
   waiver of appeal must be honored. If the agreement is
   involuntary or otherwise unenforceable, then the de-
   fendant is entitled to appeal.
United States v. Wenger, 58 F.3d 280, 282 (7th Cir. 1995); see also
United States v. Sines, 303 F.3d 793, 798 (7th Cir. 2002). Thus, in
Sura we permitted an appeal despite a waiver, and ultimately
set aside the defendant’s underlying guilty plea, because we
determined that the plea and related waiver were not
12                                                   No. 16-3583

intelligently and voluntarily made. 511 F.3d at 657–63. The
same principle holds here. Olson is entitled to challenge his
plea on knowledge and voluntariness grounds despite the
plea waiver. As we already have discussed, we have no
confidence that Olson again entered into the plea agreement
on September 9 and, if so, that he did so knowingly and
intelligently.
    We also reject the government’s contention that Olson
waived his appellate rights by supposedly declining an op-
portunity to withdraw his guilty plea on September 9. As the
government notes, while we treat a failure to file a motion to
withdraw a guilty plea as a forfeited claim reviewed for plain
error, an “intentional relinquishment or abandonment of a
known right” to withdraw a guilty plea “is properly charac-
terized as a waiver of that right” and not subject to appeal.
United States v. Davis, 121 F.3d 335, 338 (7th Cir. 1997). The
government argues that Olson’s case is just like Davis, which
applied the latter standard. In Davis, the defendant had ob-
tained new counsel after pleading guilty. Id. at 336. When the
new attorney expressed dissatisfaction with his predecessor’s
performance, albeit without providing an explanation, the
court offered Davis the opportunity to withdraw his guilty
plea. Id. After repeated discussion, Davis and his attorney de-
clined that offer, and the case proceeded to sentencing. Id. at
336–37. On direct appeal, Davis sought to withdraw his guilty
plea, arguing for the first time that his original lawyer was
conflicted and that his plea was not voluntary and knowing.
Id. at 335. This court treated the issue as waived:
     With the advice of counsel and ample opportunity to
     reflect on the matter, Mr. Davis declined the district
     court’s invitation to withdraw his guilty plea; he is not
No. 16-3583                                                   13

   entitled to a second bite of the apple by raising on ap-
   peal the very matter that he told the district court he
   did not want to raise.
Id. at 338–39. The result in Davis was not driven by the defend-
ant’s failure to take the opportunity to withdraw his plea. Ra-
ther, the defendant, having obtained new representation, de-
liberately bypassed the chance to withdraw his plea with full
knowledge that the guilty plea was tainted by the misconduct
of his former attorney. Nothing prevented him from starting
anew.
    In stark contrast to Davis, when Olson entered a guilty
plea on September 9 the district court’s Rule 11 errors had not
yet been cured. In fact, the district court had yet to commit
them. The government’s argument to the contrary again rests
on the mistaken premise that Olson simply withdrew his
August 26 motion and elected to persist with his April 6 plea.
We have rejected that characterization of the proceedings.
Once the district court ruled on the motion to withdraw the
guilty plea on August 26, there was no guilty plea left on the
table. On September 9, Olson offered a new guilty plea, but
the district court never explored the new plea as required by
Rule 11. It never afforded Olson the opportunity to withdraw
the September 9 plea, and thus Olson could not have waived
his right to do so.
                              III
    Courts’ rulings have meaning. Had the district court opted
to take Olson’s August 26 motion under advisement, then
when Olson re-appeared on September 9 and stated that he
was willing to admit his guilt we might have a different case.
But it did not. It granted his motion to withdraw the guilty
14                                                No. 16-3583

plea. At that point both the plea and the accompanying agree-
ment were off the table. When Olson had another change of
heart, the district court was obliged to conduct a new Rule 11
inquiry. For all we know, the government might have taken
the position that it would not renew the earlier agreement and
wished to pursue the additional counts of the indictment. Al-
ternatively, the government might have been willing to pick
up where it left off in August.
    We REVERSE Olson’s conviction and REMAND his case to the
district court for further proceedings consistent with this
opinion. Olson must have the opportunity to enter a new plea,
either guilty or not guilty, and the government is free to de-
cide whether to pursue a plea agreement. In light of this deci-
sion, we have no occasion to consider any procedural short-
comings in Olson’s sentencing.
