Matter of Pickering: The Two-Track Test for Vacated Convictions

Matter of Pickering is the 2003 Board of Immigration Appeals decision that decides when a vacated criminal conviction still counts against a noncitizen. The rule is a two-track test: if a court threw the conviction out because of a legal defect in the original criminal case, it no longer exists for immigration purposes. If a court threw it out for rehabilitation or to spare the person from deportation, the conviction remains, and the person can still be removed.¹

The Two-Track Test

The framework interprets Section 101(a)(48)(A) of the Immigration and Nationality Act, which defines a “conviction” as a formal judgment of guilt or, where formal adjudication is withheld, a finding of guilt paired with some form of punishment.² Pickering sorts every vacatur into one of two categories:

Vacatur based on a legal defect in the underlying criminal case — ineffective assistance of counsel, a constitutional violation, a statutory error, or another procedural or substantive flaw — eliminates the conviction for immigration purposes.¹
Vacatur granted for rehabilitation or to avoid immigration consequences leaves the conviction in place. The person is still “convicted” for federal immigration purposes even though the state or foreign court has wiped the record clean.¹

USCIS applies this rule directly. Its Policy Manual instructs adjudicators that a judgment vacated because of constitutional defects, statutory defects, or pre-conviction errors affecting guilt is not a conviction, while a judgment vacated for rehabilitative purposes or to avoid immigration consequences remains one. The manual also treats a vacatur based on the criminal court’s failure to warn about immigration consequences, under Padilla v. Kentucky, as a substantive vacatur, because it addresses a defect in the underlying proceeding.³

The Facts of the Pickering Case

Christopher Pickering, a Canadian citizen, was convicted in Chatham, Ontario, in 1980 of unlawful possession of LSD under Canada’s Food and Drugs Act. The sentence was a $300 Canadian fine or 30 days in custody. He also had earlier Canadian convictions from the late 1970s for taking a vehicle without consent and for assault causing bodily harm, and he received a Canadian pardon for all three offenses in 1996.¹

Pickering applied for adjustment of status in March 1993. The application was denied because of the 1980 drug conviction, and removal proceedings began in August 1998. In June 1997, before the immigration judge ordered him removed in September 1999, the Ontario Court of Justice quashed the 1980 conviction. Pickering argued to the BIA that the quashed conviction could no longer support removal.¹

The BIA held that the Canadian court had quashed the conviction “solely for immigration purposes” to clear his path to permanent residence in the United States, not because of any defect in the 1980 proceedings. Under the new framework, that meant the conviction still stood, and the Board affirmed the removal order.¹

The Sixth Circuit reversed in 2006. It accepted the BIA’s legal framework but faulted the application. The record lacked transcripts of the Canadian hearing, and the Canadian court had cited specific legal authority — Section 24(1) of the Canadian Charter of Rights and Freedoms — which the Sixth Circuit read as a presumption that the court acted to remedy a legal defect. The court also held that the government bears the burden of proving by clear and convincing evidence that a vacated conviction remains valid for immigration purposes, and remanded with instructions to terminate removal proceedings.⁴

Proving Which Side of the Line a Vacatur Falls On

In practice, the harder question is often evidentiary: which category does a particular vacatur belong to, and who has to show it? The BIA’s 2024 decision in Matter of Azrag illustrates the stakes.⁵

Mogtabi Hassan Azrag had been convicted in Kansas in 2020 of two counts of theft, each carrying a 12-month sentence. He later moved to withdraw his guilty pleas, alleging inadequate advice from counsel. The Kansas court granted the motion five days after it was filed. The order stated only that the judge had reviewed the file, noted the parties’ agreement, and was “duly advised.” It cited no legal authority, made no findings about counsel’s conduct, and reached no conclusions about any constitutional violation.⁵

The BIA denied Azrag’s motion to reopen. Because the state order did not explain the basis for the vacatur, and Azrag offered no independent evidence of a legal defect beyond his own unsworn allegations, he had not carried his burden to show the vacatur was substantive. A state court’s willingness to grant a motion is not itself proof of why.⁵

The practice lesson is direct. A criminal defense lawyer trying to protect a client from immigration consequences needs the vacatur order to say, in its own words, that it rests on a constitutional, statutory, or procedural defect, supported by detailed affidavits and documentary evidence rather than bare attorney assertions. A silent order — even one that closes out the criminal case successfully — can fail in immigration court.⁶

Sentence Modifications: Matter of Thomas and Thompson

In 2019, Attorney General William Barr extended the Pickering principle beyond vacated convictions to modified sentences. Matter of Thomas and Thompson held that a state-court order changing, clarifying, or reducing a criminal sentence counts for immigration purposes only if it rests on a procedural or substantive defect in the original sentencing. A sentence reduction granted for reasons unrelated to a legal error — including one intended to help the person avoid immigration consequences — has no effect.⁷

Thomas and Thompson overruled several earlier BIA decisions that had been more generous about recognizing sentence modifications. In 2024, the Executive Office for Immigration Review issued a final rule, codified at 8 C.F.R. § 1003.55 and effective July 29, 2024, that limits the retroactive reach of the decision. The restrictive standard does not apply to sentence-modification requests filed on or before October 25, 2019, or where a noncitizen reasonably relied on the availability of such modifications when entering a guilty plea before that date.⁸ An amendment to the regulation was published in February 2026.⁹

California Penal Code § 1473.7 and Bent v. Garland

California Penal Code § 1473.7 lets people who are no longer in criminal custody move to vacate a conviction on the ground that it was “legally invalid” because the defendant did not meaningfully understand its immigration consequences when the plea was entered. The Department of Homeland Security has at times argued these vacaturs are rehabilitative and therefore fall on the wrong side of Pickering.¹⁰

The Ninth Circuit rejected that reading in August 2024. In Bent v. Garland, the court held that Section 1473.7 is not a rehabilitative statute. It is a vehicle for vacating a conviction based on a substantive or procedural error, specifically a violation of the defendant’s Fifth Amendment right to enter a knowing and voluntary plea. The BIA had “plainly erred,” the court said, in treating a state order that found a plea “involuntary” and “constitutionally deficient” as though it had been issued simply to help the person avoid deportation.¹¹

Nationwide Application and the Marquez Conde Decision

Pickering was not universally accepted at first. The Fifth Circuit’s 2002 decision in Renteria-Gonzalez v. INS held that a vacated conviction remains a conviction for immigration purposes regardless of the reason for the vacatur, reasoning that Congress had said nothing about vacated convictions when defining the term in 1996. One Fifth Circuit judge later called that result “patently absurd and constitutionally questionable” because it would keep a person removable even where an appellate court threw out the conviction for insufficient evidence or a constitutional violation.¹²

Every other circuit that considered the question — the First, Second, Third, Fourth, Sixth, Seventh, Eighth, Ninth, Tenth, and Eleventh — endorsed the Pickering two-track approach in decisions between 2005 and 2016.¹³ In 2018, the BIA resolved the split. Matter of Marquez Conde reaffirmed Pickering and applied it nationwide, including inside the Fifth Circuit. The Board invoked Chevron deference and the Supreme Court’s Brand X decision, reasoning that because the statute is silent on the effect of vacated convictions, the BIA’s interpretation could override the Fifth Circuit’s contrary reading.¹²

Where the Framework Stands After Loper Bright

The Marquez Conde extension rested on Chevron deference. In 2024, the Supreme Court overruled Chevron in Loper Bright Enterprises v. Raimondo, holding that courts must exercise independent judgment about whether an agency has acted within its statutory authority. The Court said prior decisions that relied on Chevron are not automatically overruled and remain subject to stare decisis, but the new baseline is the less deferential Skidmore standard, under which an agency interpretation carries weight only to the extent it has the “power to persuade.”¹⁴

The Department of Justice has argued that the Immigration and Nationality Act separately grants the Attorney General controlling authority over questions of law, which could provide an alternative basis for deference. Critics respond that the statute merely allocates administrative responsibility among federal agencies and does not amount to the kind of express delegation of interpretive authority that Loper Bright would credit.¹⁴

As of early 2026, Pickering remains binding BIA precedent applied nationwide. The core distinction between legal defect and rehabilitation or immigration hardship still governs how immigration judges, USCIS officers, and consular officials evaluate vacated convictions, with Marquez Conde locking in nationwide application and Thomas and Thompson extending the same logic to sentence modifications subject to the 2024 retroactivity regulation. Bent v. Garland signals that courts are willing to police how immigration authorities categorize state vacaturs, and the end of Chevron opens room for further challenges to how the BIA reads the statute.¹⁵

1
U.S. Department of Justice. Matter of Pickering, 23 I&N Dec. 621 (BIA 2003)
2
Cornell Law Institute. 8 U.S.C. § 1101(a)(48)(A) – Definition of Conviction
3
USCIS. USCIS Policy Manual, Volume 12, Part F, Chapter 2
4
FindLaw. Pickering v. Gonzales, 465 F.3d 263 (6th Cir. 2006)
5
U.S. Department of Justice. Matter of Azrag, 28 I&N Dec. 784 (BIA 2024)
6
CLINIC. BIA Explains When State Criminal Vacaturs Are Recognized in Immigration Proceedings
7
U.S. Department of Justice. Matter of Thomas and Thompson, 27 I&N Dec. 674 (A.G. 2019)
8
Immigrant Legal Resource Center. EOIR Regulation Limits Retroactivity of Matter of Thomas and Thompson
9
Cornell Law Institute. 8 CFR § 1003.55
10
Immigrant Legal Resource Center. Using and Defending California Penal Code 1473.7 Vacaturs in Immigration Proceedings
11
U.S. Court of Appeals for the Ninth Circuit. Bent v. Garland, No. 22-1910 (9th Cir. 2024)
12
U.S. Department of Justice. Matter of Jose Marquez Conde, 27 I&N Dec. 251 (BIA 2018)
13
myattorneyusa. Matter of Marquez Conde – BIA Reaffirms Nationwide Rule for Vacated Convictions
14
AILA. Thoughts on the Immigration Impact of Loper Bright Enterprises
15
Immigrant Legal Resource Center. Immigrant Post-Conviction Relief