In the

United States Court of Appeals

For the Seventh Circuit ____________________ 

No. 21-1804 

OLAWOLE OLUWAJANA, 

Petitioner, 

v.

MERRICK B. GARLAND, 

Attorney General of the United States, 

Respondent. 

____________________ 

Petition for Review of an Order

of the Board of Immigration Appeals. 

No. A061-591-186

____________________ 

ARGUED DECEMBER 1, 2021 — DECIDED MARCH 9, 2022 

AMENDED MAY 3, 2022 

____________________ 

Before MANION, BRENNAN, and JACKSON-AKIWUMI, Circuit 

Judges. 

MANION, Circuit Judge. After an immigration judge ordered him removed from the United States, Olawole Oluwajana appealed to the Board of Immigration Appeals and retained counsel to represent him. But the government was
2 No. 21-1804 

slow in providing a copy of Oluwajana’s immigration file, 

without which his attorney could not prepare a brief. The 

Board granted one extension but denied a second, suggesting 

that Oluwajana instead submit his brief with a motion seeking 

leave to file it late. When he did so, less than two weeks after 

the submission deadline, the Board denied the motion in a 

cursory—and factually erroneous—footnote. And having rejected the brief, the Board upheld the removal order without 

considering Oluwajana’s allegations of error by the immigration judge. Based on the undisputed circumstances of this 

case, we conclude that the Board abused its discretion by unreasonably rejecting Oluwajana’s brief. We therefore grant the 

petition for review, vacate the Board’s order, and remand for 

further proceedings.

Originally from Nigeria, Oluwajana became a lawful permanent resident of the United States in 2011. In 2017, he was 

convicted in Illinois state court of criminal sexual assault and

aggravated criminal sexual abuse. Based on these convictions, 

the Department of Homeland Security charged him with removability. See 8 U.S.C. § 1227(a)(2)(A)(iii) (“Any alien who is 

convicted of an aggravated felony at any time after admission 

is deportable.”). 

He was unrepresented throughout immigration court proceedings. At the final hearing, the immigration judge (IJ) 

wanted to know whether Oluwajana had been able to find an 

attorney. When Oluwajana said he had not, the IJ asked 

whether he was prepared to proceed anyway, and Oluwajana 

said he was. After confirming the state crimes of which Oluwajana was convicted, the IJ inquired whether there was any 

reason he could not return to Nigeria. Oluwajana stated that 

his entire family resided in the United States and that he 
No. 21-1804 3

believed he would be targeted by criminals upon his return to 

Nigeria. In response to the IJ, counsel for the government 

stated that she did not believe Oluwajana had a basis to file 

an “I-589,” an immigration form by which a person may request relief from an order of removal.

A few weeks after the hearing, Oluwajana was ordered removed from the United States. The IJ concluded that the state 

crimes of which Oluwajana was convicted constituted aggravated felonies and that no apparent eligibility for relief from 

removal had been demonstrated. 

Oluwajana timely appealed to the Board in June 2020. 

Three months later, he retained counsel. His attorney 

promptly requested a copy of Oluwajana’s immigration file 

from the Executive Office of Immigration Review (EOIR) and 

asked the Board to delay setting a briefing schedule until he 

received it. Eventually, the Board set a date of February 3, 

2021, for any brief to be filed. As the initial due date neared, 

Oluwajana’s counsel advised that he still had not received a 

copy of the file, including transcripts of immigration court 

proceedings. The Board extended the due date for the brief to 

February 24. As the new date approached, the EOIR still had 

not supplied the file, and Oluwajana’s counsel asked the 

Board for another extension. While the extension request was 

pending before the Board, counsel at last received the case file 

on February 16. With only a week remaining before the February 24 due date, counsel advised the Board that he could 

not properly review the materials and prepare a brief in time; 

he sought a 21-day extension.

The Board denied the second extension request. Instead, it 

informed counsel that he could submit a brief after the due 

date along with a motion for its consideration.
4 No. 21-1804 

Oluwajana’s counsel filed the brief and the accompanying 

motion on March 8, 2021—12 days after the February 24 due 

date. The brief alleged that the IJ violated Oluwajana’s due 

process rights by failing to give him an opportunity to file a 

Form I-589 and by not obtaining a knowing, intelligent, and 

voluntary waiver of the right to counsel. The brief further alleged that neither of Oluwajana’s convictions constituted aggravated felonies justifying his removal. The accompanying 

motion asserted that counsel received a copy of the immigration case file from the EOIR so late that he did not have time 

to review its contents, consult with his client, and submit a 

brief by the February 24 deadline. 

The Board issued its order in April 2021. First, it rejected 

Oluwajana’s brief in a footnote, which read in its entirety: 

The respondent filed two motions for extension 

of time to file a brief. The first was granted on

January 26, 2021; the second was denied on February 24, 2021. The respondent’s brief was due 

on February 3, 2021. It was received on March 8, 

2021. The respondent requests acceptance of the 

late-filed brief. Because the respondent’s second 

request for an extension of time was denied and 

because the respondent’s brief is untimely by 33 

days, the motion to accept the late-filed brief is 

denied.

The Board then concluded that Oluwajana’s state convictions 

rendered him removable and that he was therefore ineligible 

for asylum or withholding of removal or other relief. The 

Board dismissed Oluwajana’s appeal without directly addressing the arguments raised in his brief. This petition for 

review followed.
No. 21-1804 5

At the outset, we must ensure that we have jurisdiction to 

hear this petition. Generally, the Immigration Code authorizes our review of a final order of removal, 8 U.S.C. 

§ 1252(a)(1), but not when removal is predicated on an alien 

having committed an aggravated felony, id. § 1252(a)(2)(C). 

Yet even in the latter case, we retain jurisdiction to consider 

“questions of law.” Id. § 1252(a)(2)(D). Whether Oluwajana’s 

prior convictions count as aggravated felonies, an issue he 

raised both in this court and in the rejected brief he submitted 

to the Board, is just such a question. Eke v. Mukasey, 512 F.3d 

372, 378 (7th Cir. 2008). Because the Board’s final order of removal, among other things, concluded that Oluwajana’s state 

convictions constituted aggravated felonies, we are secure in 

our jurisdiction to review that order, including the Board’s 

preliminary decision to reject his brief arguing that the basis 

for his removal was legally erroneous. 

The parties agree that we should return this case to the 

Board for further proceedings. But Oluwajana contends that 

the Board abused its discretion in rejecting his late-filed brief 

and requests a remand with instructions that the Board accept 

it. The government, in contrast, urges a general remand to 

give the Board the opportunity to reconsider whether to accept the brief and, this time, provide an adequate explanation 

for its decision.

The rules surrounding the submission of a brief to the 

Board reflect a resolve to keep administrative proceedings 

moving expeditiously. Twenty-one days is the default period 

for all parties to file initial briefs, and reply briefs may not be 

filed as a matter of course. 8 C.F.R. § 1003.3(c)(1) (2020).* Upon 

* Section 1003.3(c)(1) was amended in 2021, but that version is not applicable in Oluwajana’s case because he filed his Board appeal before the 
6 No. 21-1804 

a showing of good cause, the Board may extend the deadline 

to file an initial brief for no more than 90 days. Id. “It is also 

the Board’s policy not to grant second briefing extension requests” except in “rare circumstances.” EOIR, Board of Immigration Appeals Practice Manual, Ch. 4.7(c)(i)(A) & (B) (updated 

Jan. 8, 2021). But, as most relevant here, the rules provide that, 

“[i]n its discretion, the Board may consider a brief that has 

been filed out of time.” Id. Given that the issue is decided by 

the Board on a discretionary basis, we unsurprisingly review 

the denial of a motion to file a late brief for abuse of that discretion. Dakaj v. Holder, 580 F.3d 479, 481 (7th Cir. 2009). 

Deferential though that standard is, however, the Board 

must still exercise its discretion in a reasonable manner. To 

that end, this court must “ensure that the Board’s legal interpretations stay within the boundaries permitted to it and that 

it has not unreasonably failed to consider relevant factual information” presented in the record before it. Chowdhury v. 

Ashcroft, 241 F.3d 848, 852 (7th Cir. 2001). 

The Board provided only two reasons for denying Oluwajana’s motion to submit a brief out of time: (1) the second 

request for an extension of the briefing deadline was denied, 

and (2) the brief was received 33 days late. Neither basis supports the Board’s decision.

First, the mere fact that the Board denied a second extension request cannot justify the rejection of a late brief. Although the agency’s regulation does not explicitly limit the 

amendment took effect. See 85 Fed. Reg. 81,588, 81,588 (Dec. 16, 2020). At 

present, the amendment’s enforcement is preliminarily enjoined. See Centro Legal de la Raza v. Exec. Off. for Immigr. Rev., 524 F. Supp. 3d 919 (N.D. 

Cal. 2021).
No. 21-1804 7

number of extensions of the briefing deadline, the Board’s 

Practice Manual makes clear that a second extension request 

will usually be denied. Yet the regulation does say that the 

Board “may consider a brief that has been filed out of time.” 

8 C.F.R. § 1003.3(c)(1) (2020) (emphasis added). Thus, the 

Board’s rules envision that a late brief may be accepted even 

though a second extension of the briefing deadline was denied. It was nonsensical for the Board to deny Oluwajana permissible relief because he was not first granted a different 

kind of relief that the Board rarely permits. We will not sustain a decision based on the Board’s interpretation of its rules 

that causes “unreasonable, unfair, and absurd results.” Chowdhury, 241 F.3d at 853. 

Next, and more obviously, the Board clearly erred in finding that Oluwajana submitted his brief 33 days late. After the 

Board granted the initial request to extend the briefing deadline, the due date was February 24, 2021, not February 3. So, 

when Oluwajana submitted his brief on March 8, it was only 

12 days past due, not the month and more stated in the 

Board’s order. The Board abuses its discretion when it exercises that discretion based on factual determinations “contrary to the detailed evidence in the record.” Siddiqui v. Holder, 

670 F.3d 736, 746 (7th Cir. 2012). 

To its credit, the government does not defend the Board’s 

decision. Rather, without confessing error, the government

urges us to remand the matter for the Board to reconsider 

whether to accept Oluwajana’s brief. When the government 

requests a general remand and that request is opposed by the 

petitioner, we will grant the request “only when there is a persuasive reason to do so.” W.G.A. v. Sessions, 900 F.3d 957, 963

(7th Cir. 2018). We discern no such reason here. 
8 No. 21-1804 

This is not a case where the Board’s decision to reject a late 

brief turned on questions of disputable fact, such as whether 

an individual in removal proceedings received notice of the 

Board’s briefing schedule, see Dakaj, 580 F.3d at 482–84, or 

whether lateness should have been excused based on a totality of subjective factors, like a petitioner’s “pro se status, education, [or] language skills,” Gutierrez-Almazan v. Gonzales, 

491 F.3d 341, 344 (7th Cir. 2007). In such cases, we remanded 

because the Board had yet to fulfill its obligation “to consider 

all relevant information,” and we were persuaded that the 

Board could—“at least in the first instance”—potentially justify its rejection of a brief. Dakaj, 580 F.3d at 483–84. 

In the present case, the salient facts are undisputed. The 

government failed to provide Oluwajana’s counsel with a 

copy of his immigration file—including the transcripts of immigration court proceedings—until February 16, 2021. This 

was almost two weeks after the initial deadline set by the 

Board to file an administrative brief, a brief that could not 

have been filed without review of the file. Yet, less than three 

weeks after the EOIR finally provided a copy of the file, counsel drafted a brief and filed it with the Board, a mere 12 days 

past the revised due date. That is, the delay resulted principally (if not entirely) from the tardiness with which the government fulfilled its obligation to provide Oluwajana’s counsel critical information. And counsel, in turn, acted expeditiously when that information was received.

On these facts, any reasonable exercise of discretion required acceptance of Oluwajana’s brief. Thus, we will not order a general remand solely for the Board to consider again 

the uncontested record already before it. At the same time, we 

decline to address Oluwajana’s allegations of error by the IJ. 
No. 21-1804 9

Those contentions are best addressed in the first instance by 

the Board, which will now have the benefit of Oluwajana’s 

briefed arguments. 

We are mindful that the abuse-of-discretion standard is 

deferential and that deadlines are necessary for the operation 

of the immigration system, which we have acknowledged is 

“overburdened.” Vidinski v. Lynch, 840 F.3d 912, 918 (7th Cir. 

2016). But the Board’s own rules contemplate that, deadlines 

notwithstanding, it is sometimes appropriate to accept a latefiled brief. Based on the present circumstances, we conclude 

that this is one of those times. 

The Board clearly abused its discretion in denying Oluwajana’s motion to file his brief out of time; the brief must be 

accepted. Accordingly, we GRANT the petition for review, 

VACATE the Board’s order, and REMAND for further proceedings consistent with this opinion.