Motion to Vacate a Guilty Plea in Massachusetts — Padilla, Clarke, and G.L. c. 278, § 29D

You pleaded guilty. Your lawyer told you it would be fine. Now you are facing deportation — or you are living under its shadow every day, afraid to travel, unable to renew your green card, cut off from a path to citizenship.

You may have a remedy. Massachusetts law — and federal constitutional law — gives non-citizen defendants the right to seek to undo a guilty plea when their attorney failed to advise them of its immigration consequences. This process is called a motion to vacate. When it succeeds, the conviction is erased and the client has a chance to resolve the case in a way that protects their right to remain in the United States.

It is not easy. It is not guaranteed. But it is possible — and at Erkan & Sullivan, it is work we do every day. Attorney Murat Erkan teaches continuing legal education courses to other Massachusetts attorneys on this precise subject. We have obtained vacaturs in cases where prior counsel failed, and we have done it by doing the work that other attorneys either did not know how to do or did not do at all.

Call First: If you or a family member pleaded guilty to any criminal charge in Massachusetts and you are not a United States citizen, call us at (978) 474-0054 before you do anything else. The immigration consequences of a conviction can be permanent. Time matters.

Why Your Prior Lawyer May Have Gotten It Wrong

Defense attorneys in Massachusetts are required under the Sixth Amendment and Article 12 of the Massachusetts Declaration of Rights to advise non-citizen clients of the specific immigration consequences of a guilty plea. This has been the law since the United States Supreme Court’s landmark decision in Padilla v. Kentucky, 559 U.S. 356 (2010).

Before Padilla, courts treated immigration consequences as “collateral” — outside the criminal lawyer’s responsibility. Padilla changed that entirely, recognizing that deportation is often the most important consequence of a plea. As the Supreme Court wrote, it is “an integral part — indeed, sometimes the most important part — of the penalty that may be imposed on noncitizen defendants who plead guilty to specific crimes.”

The Massachusetts Supreme Judicial Court followed in Commonwealth v. Clarke, 460 Mass. 30 (2011), applying the same rule under Article 12. The SJC has reinforced and extended this protection in a series of decisions, including Commonwealth v. DeJesus, 468 Mass. 174 (2014), Commonwealth v. Lavrinenko, 473 Mass. 42 (2015), and Commonwealth v. Lys, 481 Mass. 1 (2018).

What Most Defense Attorneys Miss: A general warning is not enough. Murat teaches this point in his CLE programs and it is consistently missed by defense attorneys: telling a client that a conviction “might” affect their immigration status, or simply reading the tender of plea form, does not satisfy the constitutional duty. Counsel must advise the client of the specific consequences flowing from the specific charge to which they are pleading. If that advice was incorrect or incomplete, it was constitutionally deficient.

In our experience handling post-conviction immigration cases, the most common failures by prior counsel include:

• Telling a client that “no jail time means no immigration problem” — this is flatly wrong and has been for decades.
• Treating a continuance without a finding (CWOF) as avoiding a conviction — a CWOF is a conviction for federal immigration purposes.
• Telling a client that immigration consequences “might” be an issue without specifying that the particular plea made deportation mandatory.
• Failing to explore alternative dispositions — including guilty filed, pretrial probation, or charge restructuring — that could have achieved the same criminal law result without immigration consequences.
• Failing even to ask whether the client was a citizen, and therefore never triggering any immigration analysis at all.

The Two Routes to Vacating a Plea: Padilla/Clarke and G.L. c. 278, § 29D

Route 1: Padilla/Clarke — Ineffective Assistance of Counsel

The primary route for vacating a plea on immigration grounds is a motion for a new trial under Mass. R. Crim. P. 30(b), arguing ineffective assistance of counsel under Padilla and Clarke. To succeed, you must establish two things:

1. Deficient performance — that prior counsel failed to give specific, accurate advice about the immigration consequences of the plea, or gave affirmatively wrong advice.
2. Prejudice — that but for the deficient advice, there is a reasonable probability that a reasonable person in your circumstances would have made a different decision.

There is no strict time limit on filing a Rule 30(b) motion. However, delay matters — witnesses become unavailable, memories fade, and a motion filed years after the plea requires a compelling explanation for the timing. The moment a client learns their conviction carries immigration consequences is typically when the clock starts.

Route 2: G.L. c. 278, § 29D — Failure of the Plea Judge To Advise

Massachusetts General Laws chapter 278, section 29D requires the plea judge to advise every defendant who is not a citizen of the United States that their plea “may” result in deportation, exclusion, or denial of naturalization. When that advice was not given — or was given incorrectly — the statute provides a separate, independent basis for withdrawal of the plea.

Section 29D motions are distinct from Padilla motions and carry a different standard. The defendant must show that they did not receive the required warning and that they would not have pleaded guilty had they been properly advised.

Strategic Note: Both routes can be pursued simultaneously, and often are. In practice, the Padilla/Clarke route is the more powerful of the two because it targets the specific legal advice that drove the plea decision. Section 29D is a useful additional ground when the plea record shows the judge’s warning was absent or inadequate.

Proving Prejudice: The Non-citizen Calculus

The prejudice showing is where most motions succeed or fail. Massachusetts courts have been explicit that the standard must account for the fundamentally different situation a non-citizen faces compared to a citizen.

As the SJC wrote in Commonwealth v. DeJesus: “For a noncitizen defendant, preserving his right to remain in the United States may be more important to [him] than any jail sentence.” A court evaluating prejudice must assess the plea offer through that lens — not through the lens of what a citizen facing the same charges would have done.

The SJC has identified three ways to establish prejudice, and a defendant need only prove one:

Importantly, courts look at the circumstances as they existed at the time of the plea — not as they are today. The question is what a reasonable person in the defendant’s position would have done then, with correct advice, not what makes sense now with the benefit of hindsight.

On the question of whether it was reasonable to reject the plea, the United States Supreme Court held in Lee v. United States, 582 U.S. 1958 (2017), that a defendant’s deep connections to the United States can make it rational to reject a plea and go to trial even when the prospects of acquittal were grim — because any chance of acquittal preserved what the defendant most valued.

The Guilty Filed Disposition: The Option Prior Counsel Likely Never Considered

One of the most consequential — and most overlooked — tools for protecting a non-citizen client in a criminal case is the guilty filed disposition. Understanding why it matters is essential to evaluating whether a vacatur motion has merit.

Under federal immigration law, a conviction requires two elements: (1) a formal judgment of guilt, or a plea of guilty; AND (2) some form of punishment, penalty, or restraint on liberty. Matter of Ozkok, 19 I&N Dec. 546 (BIA 1988); 8 U.S.C. § 1101(a)(48)(A).

When a case is placed on file following a guilty plea, sentencing is held in abeyance indefinitely. Because no punishment, penalty, or restraint is imposed, a guilty filed disposition does not constitute a conviction for federal immigration purposes. The criminal exposure — the requirement to return for sentencing if the defendant reoffends — remains, but the immigration consequence is eliminated entirely.

The Insight That Changes Everything: A two-year administrative probationary plea and a guilty filed plea can be functionally identical from the Commonwealth’s perspective — the defendant is monitored, must stay out of trouble, and faces the underlying sentence if they reoffend. But one destroys the client’s immigration status and the other does not. The only difference is whether counsel knew to ask for it.

In building a vacatur motion, we analyze whether a guilty filed disposition was realistically available in the original case. If it was — and in many cases it is, particularly for first-time offenders in relatively minor matters — that becomes a powerful showing on the prejudice prong: a better plea was available, prior counsel was unaware of it, and but for that ignorance the client would never have been exposed to deportation.

Shepard Documents: Controlling What the Immigration Court Sees

In the context of both avoiding immigration consequences at the time of a plea and challenging them afterward, understanding the “record of conviction” — known as the Shepard documents — is essential.

When an immigration court evaluates whether a Massachusetts conviction triggers deportation, it is limited to a specific set of documents: the charging instrument, the plea colloquy, any signed plea agreement or waiver form, the judgment, and the factual basis for the plea. Shepard v. United States, 544 U.S. 13 (2005).

This means that facts outside those documents — even if they were the actual basis for the prosecution — generally cannot be used by the government to establish an immigration consequence. In practice, this creates structuring opportunities:

• Keep the type of controlled substance out of the record of conviction where possible — under Mellouli v. Lynch, 575 U.S. 798 (2015), a drug paraphernalia conviction that does not specify a federally scheduled substance may not trigger the controlled substance ground of deportability.
• For gun charges, a plea to ammunition possession rather than firearm possession may avoid the firearms ground of deportability under 8 U.S.C. § 1227(a)(2)(C), which requires that the firearm be an element of the offense of conviction.
• Where the length of sentence controls whether a conviction is an aggravated felony (e.g., crimes of violence, theft), ensure no sentence — suspended or imposed — is one year or more. Consider “from/after” sentences, each under one year.
• Avoid domestic relationship language in the record of conviction where doing so would trigger the domestic violence ground of deportability.

In post-conviction vacatur motions, an analysis of the Shepard documents is also critical to understanding whether the conviction as entered actually triggers the immigration consequence the client is facing — or whether there is an argument that it does not.

How We Build the Motion: What Separates Winning from Losing

The most important thing Murat tells lawyers at his CLE programs is this: boilerplate motions fail. Motions that tell the client’s story succeed.

A motion to vacate a guilty plea is not a form document. It is a case — built from investigation, developed through affidavits, and presented to a judge who will be making a credibility determination on papers. Every element of that case must be constructed with care.

Step 1: Understand the Client’s Full Story

The prejudice analysis requires knowing who your client was at the time of the plea — not who they are today. How long had they been in the United States? What family did they have here? What had they built? What did the country of origin hold for them? What did they tell prior counsel about their immigration concerns? The answers to these questions are the foundation of the special circumstances showing.

Step 2: Investigate Prior Counsel — In Writing, Always

Every communication with prior counsel must be in writing. This serves two purposes: it creates a paper trail that documents your efforts to obtain their cooperation, and it may reveal exactly how little they understood about their client’s immigration situation.

Many attorneys who gave deficient immigration advice become defensive when asked about it. In our experience, their resistance often contains the most important clues. If a lawyer says “I gave him the warning,” that is a red flag — the required advice was specific and individualized, not a generic warning. If a lawyer says “you don’t want my affidavit,” that is an even clearer signal that their recollection does not help the Commonwealth’s case.

We ask prior counsel to describe, in detail: their understanding of the client’s immigration status; what immigration consequences they identified as flowing from the specific charge; what alternative dispositions they explored; and what they told the client. A lawyer who claims to have given competent immigration advice will have specific answers to all of these questions. A lawyer who did not will not.

Step 3: Obtain an Affidavit From Prior Counsel — or Document Why You Cannot

Massachusetts courts have consistently held that the absence of a supporting affidavit from prior counsel weighs against a motion to vacate. Commonwealth v. Martinez, 86 Mass. App. Ct. 545 (2014). But courts have also held that where a defendant has made documented, good-faith efforts to obtain an affidavit and counsel has refused to cooperate, the absence of the affidavit may itself support the inference that “a lawyer who is aware that his assistance . . . was less than exemplary might very well be reluctant to describe that lapse in an affidavit intended for submission to a court.” Id. at 551.

When prior counsel refuses to cooperate, we document every attempt — letters by certified mail, emails, follow-up correspondence — and submit that documentation with an affidavit from current counsel attaching the paper trail. The refusal becomes evidence.

Step 4: Build a Complete, Non-Conclusory Affidavit from the Client

The Commonwealth’s default response to any vacatur motion is that the defendant’s affidavit is “self-serving” and should be rejected without a hearing. Courts are too ready to accept this argument. The answer is not to acknowledge it — it is to preempt it.

A compelling affidavit does not just say “I would not have pleaded guilty.” It explains why, in specific and verifiable detail: what the client told prior counsel about their concerns; what they understood the plea to mean; what their life in the United States looked like at the time; and why a reasonable person in their circumstances would have made a different choice with accurate advice.

As Murat teaches in his CLE: ask why your LPR client would accept a CWOF to drug distribution if they understood it was a conviction for immigration purposes. A CWOF might preserve their employment record — but it mandates removal. Why would someone care about their employment prospects in a country from which they are about to be deported? That question, answered well, defeats the self-serving label.

Step 5: Corroborate Wherever Possible

Commonwealth v. Goodreau, 442 Mass. 341, 354 (2004), holds that courts may weigh negatively the “suspicious failure to provide pertinent information from an expected and available source.” In the typical Padilla case, the only witnesses to the attorney’s advice are the client and the lawyer. But corroboration from other sources — family members who witnessed courthouse conversations with prior counsel, immigration attorneys who advised the client after the plea and can describe what they learned, colleagues or employers who can speak to the client’s roots in the United States — adds weight that a self-serving label cannot diminish.

Step 6: Address the Prosecution’s Interest — or Lack of It

One of the most underutilized arguments in vacatur litigation is the challenge to the prosecution’s actual interest in opposing the motion. Once the sentence has been served, the Commonwealth’s interest in maintaining a conviction is often minimal. If the original disposition was a CWOF, the end result of the case — had everything gone properly — was dismissal. The prosecution has no conviction to preserve.

If the conviction is old enough to be eligible for sealing under Massachusetts law, there is a strong argument that the legislature has already determined it is no longer relevant to the public interest. Preserving it to mandate the deportation of someone who has rebuilt their life in the United States serves no legitimate penological purpose.

We make these arguments directly in our motions, and we engage prosecutors proactively — explaining not just the law but the equities. Some of our best results in this area have come from prosecutors who, when presented with a complete picture of the case and the client, chose not to oppose.

What This Work Looks Like in Practice

CASE RESULT: Motion to Vacate Granted — Drug Distribution, Peabody District Court

A lawful permanent resident from the Dominican Republic who had lived in the United States for nearly a decade pleaded guilty in 2003 in an Essex County District Court to one count of heroin distribution, receiving an eight-month suspended sentence. His attorney — like most defense lawyers of that era — operated under the mistaken belief that a sentence under one year was a universal shield against deportation. It is not. Drug distribution convictions become aggravated felonies under federal immigration law without regard to the length of the sentence imposed. A companion conviction in Lynn District Court had already been vacated by a judge who found that “better work may have allowed defendant to remain without fear of deportation” — and who identified the failure to file available pretrial motions as part of the deficiency. We filed a motion to vacate the Peabody conviction based on the same erroneous advice, supported by an affidavit from plea counsel’s law partner confirming that the “under a year” misunderstanding was standard practice at the firm during that period.

Result: Motion allowed. The case was resolved with a guilty filed disposition — the same immigration-safe resolution that had been available in 2003, and that competent counsel would have pursued. Our client, the father of a U.S.-citizen daughter and three additional children, can remain in the United States.

Questions People Ask Us About Motions To Vacate

How do I know if my prior attorney gave me bad advice?

If any of the following are true, you may have been given deficient advice: you were told that no jail time meant no immigration problem; you were told your case “probably” wouldn’t affect your immigration status without a specific explanation of why; you were never asked about your immigration status at all; you were told there was no way to avoid immigration consequences when a guilty filed or other disposition was available; or you pleaded guilty without any discussion of immigration consequences whatsoever.

Does it matter that the judge warned me at the plea hearing?

Not in the way the Commonwealth will argue. The SJC has repeatedly held that a judge’s generic alien warning does not substitute for defense counsel’s constitutional duty to provide specific, individualized advice. Clarke, 460 Mass. at 48; DeJesus, 468 Mass. at 183. In practice, when a defense attorney specifically tells a client that the judge’s warning does not apply to their situation, a reasonable client will follow their attorney’s advice — not the court’s boilerplate. The SJC understands this reality.

What if prior counsel claims they did advise me?

This is a credibility dispute, and the answer is not to give up — it is to demand a hearing. Courts may not simply prefer a prior attorney’s self-serving affidavit over a defendant’s without making credibility findings. If the evidence conflicts, the appropriate resolution is an evidentiary hearing at which both sides can testify and be cross-examined. We litigate hard for evidentiary hearings in contested cases, and we have the investigative depth — including bar discipline records, documented inconsistencies, and corroborating witnesses — to challenge prior counsel’s account.

My first motion was denied. Can I file again?

Yes, in appropriate circumstances. Mass. R. Crim. P. 30(b) permits successive motions when there is a new factual basis that was not presented in the first motion — and that could not have been presented with reasonable diligence. Prior counsel’s subsequent bar discipline, newly obtained affidavits, newly discovered inconsistencies in prior counsel’s account, or a first attorney’s failure to conduct the investigation that would have revealed available dispositions can all constitute grounds for a second motion. At Erkan & Sullivan, PC, we have won cases where previous lawyer’s efforts failed, but our more robust motions and investigation carried the day.

What happens if the motion is granted?

If the court vacates your plea, you are returned to the position you were in before the plea — the case is live again and you face the original charges at trial. This sounds daunting, but several things often follow: the prosecution may choose not to re-try the case, particularly if the original evidence was weak or if significant time has passed; we may be able to negotiate an immigration-safe resolution of the case now that the stakes are understood; or we may take the case to trial. The conviction that was destroying your immigration status is gone. What comes next is a new case, handled correctly from the start.

What does the process cost and how long does it take?

Every case is different. Post-conviction immigration work is investigation-intensive — obtaining affidavits, researching bar records, analyzing the record of conviction, and building the legal argument takes time. We discuss fees transparently at the initial consultation. As for timing: once a motion is filed, courts typically schedule a hearing within several months, though contested matters can take longer. If you are already in removal proceedings, timing is critical and we work to move as quickly as the case requires.

Talk to Erkan & Sullivan

If you plead guilty to a Massachusetts criminal charge and you are not a United States citizen — or if someone in your family did — you need an attorney who understands both the criminal law and the immigration law, and who will do the investigative work that gives a motion to vacate the best possible chance of succeeding.

Attorney Murat Erkan teaches this area of law to his peers. He has been doing this work for decades — including in cases where prior counsel failed and we had to undo the damage. Attorney Ryan Sullivan brings appellate depth and an understanding of how these issues develop through the Massachusetts courts.

If you have a case worth pursuing, we will tell you honestly. Contact us today.