IN THE SUPREME COURT OF IOWA

No. 18–0184

Filed March 8, 2019

STATE OF IOWA,

Appellee,

vs.

BERNARD ANTHONY SMITH,

Appellant.

Appeal from the Iowa District Court for Story County, Timothy J. 

Finn, Judge.

A defendant challenges his sentence as a habitual offender and the 

imposition of restitution and a fine. AFFIRMED IN PART, REVERSED IN 

PART, AND REMANDED.

Mark C. Smith, State Appellate Defender, and Maria Ruhtenberg, 

Assistant Appellate Defender, for appellant.

Thomas J. Miller, Attorney General, Kyle Hanson, Assistant Attorney

General, Jessica Reynolds, County Attorney, and Timothy C. Meals and 

Shawna Johnson, Assistant County Attorneys, for appellee.
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WIGGINS, Justice. 

The defendant was convicted of second-degree burglary and 

stipulated to being a habitual offender. The court sentenced the defendant 

as a habitual offender, ordered restitution, and imposed a fine. On appeal, 

we conclude the stipulation was not knowingly and voluntarily made 

because the stipulation proceedings did not comply with the requirements 

of State v. Harrington, 893 N.W.2d 36 (Iowa 2017). Accordingly, we must 

reverse the habitual offender judgment, the defendant’s sentence, and 

remand the case for further proceedings consistent with Harrington. See 

id. at 45–46. We affirm the uncontested judgment of guilt on seconddegree burglary.

I. Facts and Proceedings.

On September 27, 2017, the State charged Smith with burglary in 

the second degree in violation of Iowa Code sections 713.1 and 713.5 

(2017), a class “C” felony, and being a habitual offender in violation of 

section 902.8. Following Smith’s not-guilty plea, a bifurcated trial on the 

burglary charge began on November 28. 

While the jury was in deliberations, Smith’s counsel informed the 

court that Smith would stipulate to the predicate priors for the habitual 

offender charge. The following exchange occurred:

[DEFENSE COUNSEL]: Your Honor, I just discussed 

with my client about the sentencing enhancement charge on 

the Trial Information of offense of habitual offender and my 

client has decided that he will withdraw his request for a 

bifurcated trial and will stipulate to the priors for that 

particular section should the jury return a guilty verdict that 

it would be applicable to.

THE COURT: Okay. Very well. Mr. Smith, is that 

correct?

THE DEFENDANT: Yes, sir.
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THE COURT: I told you earlier about the ramifications 

of doing that. It’s your decision and you voluntarily decided 

that you will stipulate to the habitual offender element of the 

trial?

THE DEFENDANT: Yes.

THE COURT: Okay. All right. Thank you. Anything 

further on behalf of the State?

[PROSECUTOR]: No, Your Honor.

THE COURT: Thank you.

[DEFENSE COUNSEL]: Thank you, Your Honor.

Subsequently, the jury returned a verdict finding Smith guilty of 

burglary in the second degree. After the court scheduled sentencing, 

further discussion regarding Smith’s stipulation occurred:

[DEFENSE COUNSEL]: Your Honor, [the prosecutor] 

brought to my attention a case State v. Harrington, 893 

N.W.2d 36. It concerns a Defendant making admissions to 

the habitual offender without the State having to prove it up 

and the issue of bringing it up in a motion in arrest of 

judgment or making an adequate record.

I believe we probably have an adequate record but just 

to be safe, it probably would be best to maybe supplement the 

record a little bit at this time, that the Defendant did freely 

voluntarily stipulate to the priors of the habitual offender.

THE COURT: All right. I think we did that. But you’re 

in agreement on that; aren’t you?

THE DEFENDANT: Yes.

THE COURT: All right. Thank you. I appreciate that. 

You understand that’s voluntary on your part and you elected 

to go along with that?

THE DEFENDANT: Correct.

THE COURT: Okay. I have one last thing I need to tell 

you about. You have the right to file what’s called a motion in 

arrest of judgment. The motion has to be filed at least I think 

it’s five days or three days?

[THE PROSECUTOR]: Five days, Your Honor.
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THE COURT: Five days before the date of sentencing. I 

set your sentencing on January 16th. So if you want the 

Court to consider that, it has to be filed at least five days 

before January 16th. Do you understand that?

(At this time there is an off-the-record discussion 

between [defense counsel] and the Defendant.)

(We are now back on the record.)

[THE PROSECUTOR]: Your Honor, I think it’s forty-five 

days but no less than five days before sentencing.

THE COURT: Okay.

[DEFENSE COUNSEL]: That is correct.

THE COURT: All right. Got that?

THE DEFENDANT: Yes.

THE COURT: Okay. All right. That will conclude the 

hearing.

Thank you.

The court gave no other information on the motion and had no further 

conversation about Smith’s stipulation to the prior convictions. Smith did 

not file a motion in arrest of judgment challenging the habitual offender 

stipulation proceedings.

On January 16, 2018, the district court sentenced Smith as a 

habitual offender to incarceration not to exceed fifteen years. The court 

also imposed a fine of $1000, ordering, “The Defendant should be and is 

hereby fined in the sum of $1,000 plus a 35 percent surcharge. This fine 

and surcharge are hereby SUSPENDED.” Regarding restitution, the order 

said,

[T]he Defendant shall be required to pay the costs of this 

action, the $125 law enforcement initiative surcharge, and 

that he reimburse the state for the reasonable fees of his 

court-appointed attorney. The Defendant’s attorney is given 

10 days within which to file a statement of the legal services 

he has provided for the Defendant. All costs, surcharges, and 
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fees are due immediately and shall be considered delinquent 

if not paid within 30 days of today’s date.

On January 25, Smith appealed the court’s final order. The district court 

filed a restitution plan on March 20, ordering Smith to pay a total of 

$1434.60. 

II. Issues.

On appeal, Smith raises three issues. First, he claims the district 

court failed to comply with the Harrington requirements in accepting his 

habitual offender stipulation. Second, he claims the district court erred 

in ordering him to pay restitution in the form of attorney fees. Third, he 

claims the district court erred in imposing a fine. 

We need not reach Smith’s second or third claim because our 

resolution of the first issue will require resentencing.

III. Standard of Review.

“Claims involving the interpretation of a statute or rule are usually 

reviewed for errors at law.” Harrington, 893 N.W.2d at 41 (quoting State v. 

Kukowski, 704 N.W.2d 687, 690–91 (Iowa 2005)); see Iowa R. App. P. 

6.907. 

IV. Compliance with the Harrington Requirements.

On appeal, Smith first claims the district court failed to comply with 

the habitual offender stipulation requirements from Harrington and, 

therefore, his stipulation could not have been voluntarily and intelligently 

given. See 893 N.W.2d at 45–46. Alternatively, he contends that if he 

failed to preserve error on his Harrington challenge, his trial counsel 

provided ineffective assistance.

A. Error Preservation. In Harrington we held that “offenders in a 

habitual offender proceeding must preserve error in any deficiencies in the 

proceeding by filing a motion in arrest of judgment.” Id. at 43. However, 
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we elected to apply that rule of law prospectively such that it did not apply 

in Harrington and in other cases that preceded our Harrington decision. 

Id.; see, e.g., State v. Brewster, 907 N.W.2d 489, 493 n.3 (Iowa 2018) 

(excusing failure to comply with error preservation rule because the case 

was already on appeal at the time of the Harrington decision); State v. 

Steiger, 903 N.W.2d 169, 170 (Iowa 2017) (per curiam) (excusing failure to 

comply with error preservation rule because the rule was not in existence 

at the time). 

Smith’s habitual offender proceedings occurred several months after 

our Harrington decision, but he failed to file a motion in arrest of judgment 

to challenge those proceedings. Accordingly, this case presents the first 

opportunity, post-Harrington, for us to consider the consequences of 

failing to file a motion in arrest of judgment to challenge the habitual 

offender proceedings.

Smith claims the Harrington error preservation requirement does 

not apply here because the district court failed to adequately advise him, 

as required by Iowa Rule of Criminal Procedure 2.8(2)(d) for guilty plea 

proceedings, of his right to file a motion in arrest of judgment and of the 

consequences of failing to do so. See, e.g., State v. Meron, 675 N.W.2d 537,

541 (Iowa 2004) (noting court’s failure to inform the defendant entering 

guilty plea of those two pieces of information as required by rule 2.8(2)(d) 

excuses the defendant’s failure to challenge the guilty plea proceedings by 

filing a motion in arrest of judgment). Smith contends the requirement in 

rule 2.8(2)(d) and the error preservation exception noted in Meron should 

apply to habitual offender proceedings. See id. We agree.

We have consistently acknowledged that stipulating to prior offenses 

for purposes of sentencing enhancement is “comparable to a plea of guilty 

to support sentencing for the crime identified in the plea.” Harrington, 893 
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N.W.2d at 42; accord, e.g., Kukowski, 704 N.W.2d at 692; State v. Brady, 

442 N.W.2d 57, 58 (Iowa 1989). We have relied on this similarity to 

conclude it is appropriate to refer to our guilty plea rules when resolving 

challenges to stipulation proceedings. E.g., Harrington, 893 N.W.2d at 45 

(referring to guilty plea rules to identify the specific topics that must be 

part of the stipulation colloquy for the stipulation to be voluntary and 

intelligent); Brady, 442 N.W.2d at 58. We also relied on that similarity in 

holding that a motion in arrest of judgment must be filed to preserve those 

challenges for appeal. See Harrington, 893 N.W.2d at 42–43. Thus, we 

find it logical for us to consider the instant error preservation issue in light 

of our jurisprudence regarding error preservation in the guilty plea 

context. 

Moreover, we find the rationale for the error preservation exception 

in the guilty plea context equally applicable to the prior-offenses 

stipulation context. In State v. Worley, we first recognized the error 

preservation exception when a defendant failed to file a motion in arrest of 

judgment to challenge his guilty plea proceedings. 297 N.W.2d 368, 370 

(Iowa 1980). We noted then-rule 23(3)(a)—now rule 2.24(3)(a)—precluded 

appellate challenges to guilty plea proceedings if the defendant did not first 

challenge that proceeding in a motion in arrest of judgment. Id. But we 

also explained that now-rule 2.24(3)(a) “must be read in conjunction with” 

then-rule 8(2)(d)—now rule 2.8(2)(d)—which requires the court inform the 

defendant that challenges to the guilty plea proceedings must be raised in 

a motion in arrest of judgment and “that failure to so raise such challenges 

shall preclude the right to assert them on appeal.” Id. (quoting Iowa R. 

Crim. P. 8(2)(d) (1979)). We held, 

No defendant, however, should suffer the sanction of rule 

[2.24(3)(a)] unless the court has complied with rule [2.8(2)(d)]

during the plea proceedings by telling the defendant that he 
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must raise challenges to the plea proceeding in a motion in 

arrest of judgment and that failure to do so precludes 

challenging the proceeding on appeal. 

Id. 

As in the guilty plea context, the offender challenging the habitual 

offender stipulation proceeding must do so in a motion in arrest of 

judgment in order to preserve error on that challenge. Harrington, 893 

N.W.2d at 43. Also like in the guilty plea context, the district court is 

required to “inform the offender that challenges to an admission based on 

defects in the habitual offender proceedings must be raised in a motion in 

arrest of judgment” and “that the failure to do so will preclude the right to 

assert them on appeal.” Id. at 46. As in Worley, we must read these two 

requirements in conjunction. See 297 N.W.2d at 370. Accordingly, no 

offender in a habitual offender stipulation proceeding should suffer 

Harrington’s error preservation sanction unless the court has complied 

with its duty under Harrington to inform the offender that challenges to 

the stipulation proceedings must be raised in a motion in arrest of 

judgment and the failure to do so precludes raising those challenges on 

appeal. See Harrington, 893 N.W.2d at 45–46. 

In assessing whether the district court complied with this Harrington 

duty, we adopt the substantial compliance standard we use “in 

determining whether a trial court has discharged its duty under rule 

2.8(2)(d)” in the guilty plea context. State v. Straw, 709 N.W.2d 128, 132 

(Iowa 2006); see also State v. Fisher, 877 N.W.2d 676, 680 (Iowa 2016). 

“The court must ensure the [offender] understands the necessity of filing 

a motion to challenge a [prior-offenses stipulation] and the consequences 

of failing to do so.” Straw, 709 N.W.2d at 132.

The court’s statement that Smith had a right to file a motion in 

arrest of judgment was insufficient to comply with its duty under 
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Harrington. The court’s statement did not tie that right to the method of 

challenging the stipulation proceedings, nor did it ensure Smith 

understood that the failure to file such a motion would preclude him from 

challenging the proceedings on appeal. Cf. Straw, 709 N.W.2d at 132 

(finding substantial compliance when the court informed the defendant 

that if he wished to appeal or challenge any of the guilty plea proceedings, 

he was required to file a motion in arrest of judgment). Moreover, there 

was no written and signed stipulation to the prior offenses that otherwise 

informed Smith of this information. Cf. Fisher, 877 N.W.2d at 682 (finding 

written and signed guilty plea form failed to substantially comply with rule 

2.8(2)(d)’s requirements when it did not indicate failing to challenge the 

guilty plea proceedings in a motion in arrest of judgment waived such a 

challenge on appeal); State v. Oldham, 515 N.W.2d 44, 46–47 (Iowa 1994) 

(finding substantial compliance when the court’s otherwise insufficient 

oral colloquy was considered together with the defendant’s written and 

signed application to withdraw his not-guilty plea). Therefore, Smith is 

not precluded from challenging his prior-offenses stipulation on appeal.

B. The Sentencing Court Failed to Comply with Harrington. 

The district court failed to comply with Harrington’s requirements to 

ensure Smith’s prior-offenses stipulation in the habitual offender 

proceeding was voluntary and intelligent. Although Smith affirmatively 

responded to the court’s inquiry that Smith’s decision to stipulate to the 

habitual offender charge was voluntary, “[a]n affirmative response by the 

defendant . . . does not necessarily serve as an admission to support the 

imposition of an enhanced penalty as a multiple offender.” Harrington, 

893 N.W.2d at 45 (alteration in original) (quoting Kukowski, 704 N.W.2d 

at 692). Rather, before sentencing, the court must engage in a colloquy 
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with the offender “to ensure that the affirmation is voluntary and 

intelligent.” Id. (quoting Kukowski, 704 N.W.2d at 692).

In Harrington, we clarified the scope of this stipulation colloquy. Our 

clarification in Harrington specifically addressed prior-offenses

stipulations for habitual offender enhancement purposes, but we have 

subsequently extended the Harrington colloquy requirements to other 

sentence-enhancement, prior-offenses stipulations that occur pursuant to 

Iowa Rule of Criminal Procedure 2.19(9). E.g., Brewster, 907 N.W.2d at

494 (applying Harrington to rule 2.19(9) “proceedings in which repeat-OWIoffender enhancements are at issue”); State v. Coleman, 907 N.W.2d 124, 

147 (Iowa 2018) (applying Harrington to rule 2.19(9) proceedings involving 

“a second offense enhancement under Iowa Code section 692A.111”). The 

stipulation colloquy here fell short of the Harrington standard. 

First, the court failed to inform Smith “of the nature of the habitual 

offender charge,” “if admitted, that it will result in sentencing as a habitual 

offender for having ‘twice before been convicted of a[ny] felony,’ ” and that 

the “prior felony convictions are only valid if obtained when [Smith] was 

represented by counsel or knowingly and voluntarily waived the right to 

counsel.” 893 N.W.2d at 45 (quoting Iowa Code § 902.8 (2017)). The 

record is silent as to any determination by the court that “a factual basis 

exists to support the admission to the prior convictions.” Id. at 45–46.

Second, the court failed to inform Smith “of the maximum possible 

punishment of the habitual offender enhancement, including mandatory 

minimum punishment.” Id. at 46. Specifically, in this case, that he would 

“be sentenced to a maximum sentence of fifteen years” and that he “must 

serve three years . . . before being eligible for parole.” Id.

Third, the court did not inform Smith of the applicable trial rights 

enumerated in rule 2.8(2)(b)(4) and that no trial on the habitual offender 
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charge would take place if he admitted to the prior convictions.1 Id. Nor 

did it indicate “that the state is not required to prove the prior convictions 

were entered with counsel if [Smith] does not first raise the claim.” Id. 

Finally, the court did not adequately inform Smith that “challenges 

to an admission based on defects in the habitual offender proceedings 

must be raised in a motion in arrest of judgment” and that the “failure to 

do so will preclude the right to assert them on appeal.” Id. It is undisputed 

that the court advised Smith he had the right to file a motion in arrest of 

judgment. Nonetheless, the court did not tie the filing of such a motion 

with challenging the stipulation proceedings, and it made no indication 

that such a motion is a prerequisite to challenging the proceedings on 

appeal.

As in Harrington, the habitual offender colloquy here leaves us 

“unable to conclude [Smith’s] admission was knowingly and voluntarily 

made.” Id. at 47. Accordingly, we affirm Smith’s uncontested judgment of 

guilt for second-degree burglary, but we reverse the judgment and 

sentence of the district court and remand for further proceedings 

consistent with the stipulation requirements of Harrington, or if Smith 

denies the prior convictions or their validity, for trial on whether he 

qualifies as a habitual offender. See id. at 48.

V. Conclusion.

Smith did not file a motion in arrest of judgment to challenge his 

habitual offender stipulation proceedings as required by Harrington. 

However, the district court failed to substantially comply with its duty 

under Harrington to ensure that Smith understood the necessity of filing 

 1When Smith initially indicated he would stipulate to the prior offenses, the court 

responded by noting it had told Smith “earlier about the ramifications of doing that.” Yet,

the record does not contain or otherwise reveal the substance and scope of that earlier 

advisement.
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such a motion and that the failure to so file would preclude challenging 

the proceedings on appeal. Therefore, we excuse Smith’s failure to 

preserve error.

On the merits of Smith’s challenge to the stipulation proceedings, 

we find that his prior-offenses stipulation was not knowingly and 

voluntarily made because the stipulation proceedings fell short of 

Harrington’s requirements. Thus, we reverse the habitual offender 

judgment and Smith’s sentence and remand the case for further 

proceedings consistent with Harrington. We affirm the uncontested 

judgment of guilt on second-degree burglary.

AFFIRMED IN PART, REVERSED IN PART, AND REMANDED.

All justices concur except McDonald, J., who takes no part.