Summary

Attorney client privilege, also written attorney-client privilege, protects confidential communications between lawyers and clients, but border searches create an unusually complicated setting for those protections. Michigan attorney Amir Makled said federal agents detained him at Detroit Metro Airport, sought access to his phone, and questioned him after he returned from a family vacation. His experience raises a broader question about legal confidentiality, digital privacy, and government power at the border. This episode is part of our broader examination of civil liberties, grassroots resistance, and democratic reform.

Key Takeaway

• Attorney-client privilege does not simply disappear at the border. CBP policy provides special procedures when officers encounter material claimed to be protected by attorney-client privilege or attorney work product.
• Makled, a U.S. citizen and Michigan attorney, said he refused to provide unrestricted access to his phone but ultimately allowed agents to examine his contacts. NPR reported that he was detained for more than 90 minutes.
• Makled said he believed his legal representation of a pro-Palestinian student protester contributed to the encounter. That is his stated interpretation; CBP disputed that characterization and described the encounter as a routine inspection.
• The dispute illustrates a larger tension between border-search authority, due process, digital privacy, and the confidentiality necessary for independent legal representation.

Attorney-Client Privilege at the Border

Attorney-client privilege is designed to protect confidential communications made for the purpose of obtaining or providing legal advice. Smartphones complicate that principle because a single device can contain years of messages, documents, contacts, case files, and other potentially sensitive material.

That distinction matters at the border. CBP says its policy recognizes both basic and advanced electronic-device searches. Advanced searches involve connecting external equipment to review, copy, or analyze a device and, under current CBP policy, require reasonable suspicion of a legal violation or a national-security concern and senior-manager approval.

The episode examines those rules through Makled’s experience. According to NPR, agents requested access to his phone after he returned to Detroit with his family. Makled refused unrestricted access because, he said, the device contained confidential client information. He eventually permitted examination of his contact list. Makled argued that the encounter was connected to his representation of a student charged following a pro-Palestinian protest; CBP disputed his explanation for why he was stopped.

The unresolved policy question extends beyond a single lawyer. Border searches can bring legal privilege, digital privacy, and government investigative authority into direct conflict. The Supreme Court recognized the extraordinary quantity and sensitivity of information stored on modern phones in Riley v. California, although Riley concerned a search incident to arrest rather than the separate border-search doctrine.

That makes Episode 9 a natural companion to our examination of immigration due process and the Kilmar Abrego Garcia case. It also connects to the broader question of how political participation can be shaped by institutional pressure explored in Astroturf Politics: The Illusion of Grassroots Power.

Frequently Asked Questions

Q1: What is attorney-client privilege?

Attorney-client privilege generally protects confidential communications between a lawyer and client made for the purpose of obtaining or providing legal advice. Its application depends on the circumstances and the nature of the communication.

Q2: Does attorney-client privilege apply at the U.S. border?

Privileged information receives special treatment under CBP policy. When attorney-client privilege or attorney work product is asserted, the agency's procedures call for consultation with CBP counsel before officers proceed with potentially privileged material.

Q3: Can CBP search a lawyer’s phone at the border?

CBP asserts border-search authority over electronic devices. Its policy distinguishes between basic and advanced searches, with the latter subject to additional requirements. The constitutional limits of warrantless border searches of digital devices remain the subject of litigation and legal debate.

Q4: What happened to attorney Amir Makled?

Makled said federal agents detained him at Detroit Metro Airport after a family trip and requested access to his phone. He refused unrestricted access, citing confidential legal material, but eventually permitted agents to examine his contacts. He believes his legal work contributed to the encounter; CBP disputed that explanation.

Q5: How does this relate to due process and government overreach?

The controversy concerns how border-enforcement powers interact with privacy, confidential legal representation, and access to counsel. Civil-liberties organizations argue that broad device-search powers can chill protected activity, while CBP maintains that electronic-device searches are an important border-security and law-enforcement tool.

Related Episodes

• Astroturf Politics: The Illusion of Grassroots Power
• Deported by Mistake: Immigration Due Process and the Kilmar Abrego Garcia Case
• No Kings: America’s 3.5% Moment

Sources & Further Reading

• American Civil Liberties Union — https://www.aclu.org/news/privacy-technology/can-border-agents-search-your-electronic
• Boston Globe — https://www.bostonglobe.com/2025/04/13/metro/dhs-immigration-deportation-parole-termination/
• Boston Review — https://www.bostonreview.net/articles/lauren-carasik-government-targeting-immigration-lawyers-activists-journalists/
• Electronic Frontier Foundation — https://www.eff.org/wp/digital-privacy-us-border-2017
• NBC Boston — https://www.nbcboston.com/news/local/massachusetts-immigration-attorney-dhs-parole-termination/3684504/
• NPR — https://www.npr.org/2025/04/09/nx-s1-5357455/attorney-detained-by-immigration-authorities
• Supreme Court of the United States — https://www.supremecourt.gov/opinions/boundvolumes/573BV.pdf
• U.S. Customs and Border Protection — https://www.cbp.gov/travel/cbp-search-authority/border-search-electronic-devices
• Wired — https://www.wired.com/story/homeland-security-email-tells-a-us-citizen-to-immediately-self-deport/

1

1: advocates. Yeah, it's a concerning pattern that seems to be emerging from these sources. Exactly.

2

2: So if you're trying to cut through all the noise and just get a handle on what's really going on and why it actually matters, that's what we're aiming for in this deep dive. Our mission here is to really understand what these actions are, what the administration says the reasons are, and how the people affected see it. And crucially, we're staying focused on the constitutional issues raised, not taking political action.

3

1: Absolutely. Just laying out what the reports say.

4

2: Okay. So let's dig in. Where does this seem to start?

5

1: Well, looking at the ttownmedia.com article, it kind of points back to March 22nd. There was this memo from President Trump, and it really set a specific tone.

6

2: What did it say?

SPEAKER_01: He basically accused immigration attorneys and law firms of unscrupulous behavior. The accusation was that they were coaching clients, asylum seekers specifically, to lie to get, quote, undeserved relief.

7

2: Wow. Okay. So not just a generalization. Not just a general statement, but a direct accusation of coaching people to lie. And was there any action tied to that?

8

1: Oh, yeah. It wasn't just talk. The memo actually directed Attorney General Pam Bondi and DHS Secretary Kristi Noem to go after sanctions. Sanctions against attorneys involved in what the memo called frivolous, unreasonable, and vexatious litigation against the government.

9

2: So framing legal challenges as basically obstruction. That's a pretty strong message to send to the legal community working on these cases.

10

1: Exactly. And the Sightown Media piece, it gets into how lawyers are reacting. Attorneys in Los Angeles, for instance, they see this pretty clearly as intimidation.

11

2: To stop them defending clients, presumably.

12

1: That's their take. Yeah. To deter them from, you know, fighting hard for clients seeking asylum or facing deportation.

13

2: There's a quote in there from Meredith Brown, right? An attorney. Yes. Meredith Brown. She said something quite striking that in her, like, 25 years doing immigration law, she's never seen direct attacks like this. Not just on lawyers, but on organizations, pro-immigrant groups like Cherlie.

14

1: That really puts it into perspective. If a 25-year veteran says it's unprecedented, that suggests a real shift.

15

2: It does. And then you have Patricia Corrales, who's interesting because she used to be a DHS attorney.

16

1: Oh, right. What's her perspective?

17

2: She basically says, look, when I was at DHS for almost 20 years, it was about upholding the law, ensuring due process. Now, working privately, she's essentially telling the administration, if you break the law, if you intimidate my clients, if you do something wrong, you're going to be in trouble. And she's essentially telling the We'll see you in court.

18

1: Pretty direct challenge back. Very direct. She and others quoted there, they frame it not as politics, but as defending the Constitution. Brown even calls the Constitution a living document. They're ready to defend against what they see as the administration ignoring parts of it.

19

2: OK, so we have this high-level directive, these accusations. But then things seem to get very specific, almost bizarre, with this incident involving a Massachusetts attorney.

20

1: Ah, yes. The Nicole Maturoni case. This got picked up, by NBC, Boston, Wired, the Boston Globe. It's, well, it's quite something. She's an immigration attorney, a U.S. citizen, born and raised in Massachusetts.

21

2: All right, because of standard stuff so far.

22

1: Right. Then on Friday, April 11th, 2025, she gets this email, looks official from DHS, and it tells her, a U.S. citizen, to leave the country within seven days.

23

2: Wait, leave the country? A U.S. citizen?

24

1: Yeah, because her, quote, parole status had been terminated. It makes no sense, obviously. She doesn't have parole.

25

2: That's unbelievable. How does something like that even happen? What was her reaction?

26

1: Well, initially, she thought it must be for a client, right? It makes sense. But no, her name was the only one on it. She said the language was really threatening, kind of like spam, almost, which, you know, makes you worry about the quality control on these official notices.

27

2: Seriously? Did DHS offer any explanation for sending a deportation notice to a U.S. citizen?

28

1: They did. A senior DHS official, quoted in the Globe and NBC, Boston, blamed it on email addresses provided by non-citizens. The theory is an immigrant might give their lawyers email as a contact point.

29

2: Ah, okay, I see. So the system sends an automated notice about parole ending, and it goes to the lawyer's address instead of the actual person.

30

1: That's the explanation given. The official said CBP is monitoring and fixing these case by case.

31

2: But still, for Micaroni, it must have been alarming.

32

1: Absolutely. She called it really scary and felt it showed a serious lack of care. She even wondered if it was maybe a... ...deliberate scare tactic, just to generally make people afraid of the whole immigration process.

33

2: Yeah, you can see why she'd think that. Wired reported on his social media post, too, right? Expressing that same concern about the lack of care.

34

1: Mm-hmm, yep. She was pretty vocal about her disbelief.

35

2: And the Boston Globe piece put this email into a bigger picture, didn't it? Connecting it to parole programs.

36

1: It did. It linked these emails to a wider Trump administration pushed to cancel parole for lots of migrants admitted under Biden-era programs.

37

2: Like the CBP One app users.

38

1: Exactly. People who use the CBP One app, and also folks granted humanitarian parole, specifically mentioning Cubans, Haitians, Nicaraguans, and Venezuelans, though they noted an exception for Ukrainian and Afghan refugees.

39

2: And the numbers involved were huge, weren't they?

40

1: Staggering, really. The Globe mentioned aiming to cancel parole for over half a million from those four countries granted humanitarian parole since late 2022, plus over 900,000 who came in via the CBP One app. Wow.

41

2: That's potentially over a million people facing a sudden change in status.

42

1: It's massive. And Sarah Sherman-Stokes from BU Law, quoted in the Globe, pointed out something really concerning. A lot of these people, especially the CBP One users, they gave the government their personal info. They followed the rules to enter legally.

43

2: Right. They did what they were asked to do.

44

1: And now they get an email basically telling them to self-deport. It feels like a betrayal of that process.

45

2: Jeff Thielman from the International Institute of New England saw this happening to his clients, too.

46

1: Yeah. He told the Globe many of his clients, mostly Haitians who came legally through CBP One, got these letters. He said it caused absolute terror and confusion. They played by the rules. And now this.

47

2: It sounds incredibly destabilizing for people who thought they were following the correct procedure.

48

1: Definitely. And another Massachusetts attorney, Megan Clutt, she offered a sort of pragmatic view in the Globe piece. She basically suggested it's a pressure tactic.

49

2: How so?

SPEAKER_01: Her thinking was, maybe the administration knows deporting everyone formally through the courts is a huge logistical challenge. So send these scary letters. Maybe some people will just give up and leave on their own without needing court proceedings.

50

2: Kind of a way to bypass the system, perhaps. So you've got the rhetoric against lawyers and then these mass emails causing fear, even hitting citizens by mistake. It feels multifaceted.

51

1: It does. And then there's another really troubling incident, the detention of attorney Amir Markold. Okay.

52

2: Tell me about that one. Where did this happen?

53

1: This was reported by NPR. Markold is a Michigan-based attorney, also a U.S. citizen. He was coming back from a family vacation in the Dominican Republic, flying into Detroit Metro Airport. Right. His family gets through customs fine, but he gets pulled aside, approached by agents identified as the Tactical Terrorism Response Team.

54

2: Whoa. Okay. Tactical Terrorism Response Team. For a lawyer coming back from vacation, that sounds intense.

55

1: Markold said his heart fell into his stomach. And then, according to NPR, these border agents spent over 90 minutes trying to get him to hand over his cell phone.

56

2: His personal phone. Did they say why?

57

1: They pressured him, but he refused. His reason was crucial potential attorney-client privileged information on that phone. He couldn't just hand it over.

58

2: Right. That makes sense. Is there any context for why he might have been singled out by a terrorism response team?

59

1: Well, this is where it gets pointed. One of Markold's clients is a student who was charged, charged over involvement in a pro-Palestinian protest at the University of Michigan.

60

2: Ah. And the administration had been talking about cracking down on visa holders supporting Palestine.

61

1: Exactly. Markold himself believes that's why he was targeted. He thinks it was because he represents that student. And the attempt to get his phone wasn't about terrorism, but intimidation. A chilling effect, as he put it, to discourage lawyers from taking these kinds of politically charged cases.

62

2: Did CBP respond to that specific allegation?

63

1: NPR said they hadn't gotten a response from CBP at the time, but they noted CBP had told the Detroit Free Press earlier that electronic searches hadn't actually increased, and claims

64

2: of targeting based on politics were baseless. So, CBP says it's not happening, Maykld says it absolutely happened to them, and here's why.

65

1: Pretty much. Maykld's counterargument, reported by MTR, is basically, okay, if there was no probable cause, no warrant, no actual security threat for me, then why try so hard to get my phone? He insists it was intimidation tied to his work representing students,

66

2: immigrants, political dissenters. He also mentioned getting support from the legal community.

67

1: Yeah, he said the local bar association in the community reached out, which he felt showed people were really disturbed by this. He framed it as fundamentally against American values and the Fourth Amendment protection against unreasonable searches. An attorney being subjected to this at the border, it raises alarms. It really does. And this Maykld incident, it connects pretty directly to the wider patterns discussed. in that Boston Review article you mentioned earlier.

68

2: Right, the leaked database. Exactly.

69

1: That piece highlights a leaked Homeland Security database that specifically listed activists, journalists, and crucially, an immigration attorney named Nicole Ramos from the group Al Ocho Lado.

70

2: So confirmation that the government was keeping tabs on specific advocates.

71

1: It certainly looks that way based on the leak. The article details problems Ramos faced, like her sentry pass, that trusted traveler card being reviked with no explanation. And her colleagues at Al Ocho Lado, facing harassment, being detained, denied entry to Mexico.

72

2: And it got worse than just travel hassles, didn't it?

73

1: Much worse. The article reports their staff in Tijuana faced death threats, smear campaigns, constant surveillance for over a year. It's intense.

74

2: And were officials involved in the smear campaigns?

75

1: Disturbingly, yes. Boston Review reported CBP officials were allegedly bad-mouthing Al Ocho Lado to migrants, calling Ramos, a fake attorney who coaches lies. Which sounds awfully similar to the language in that Trump memo we started with.

76

2: It really does echo that. It's like the official rhetoric is filtering down to interactions on the ground.

77

1: It seems that way. Al Ocho Lado actually petitioned the Inter-American Commission on Human Rights because they felt the Mexican government wasn't protecting their staff, especially after they sued the Trump administration over immigration policies.

78

2: So the database itself, what was its official name? Something revealing. Yeah.

79

1: The name was San Diego Sector Foreign Operations Branch, Migrant, Caravan, FY 2019, Suspected Organizers, Coordinators, Instigators, and Media. Quite a title.

80

2: And mostly U.S. citizens on it, you said?

81

1: The article says the vast majority were U.S. citizens. It had photos, personal info, even like Ramos' travel logs.

82

2: What was CBP's reason for having this list?

83

1: Their justification, per the Boston Review, was needing to question people about border unrest in Tijuana back then.

84

2: But did that hold up?

85

1: Well, the article points out that some people harassed, later, weren't even in Tijuana during the unrest, which kind of undermines the official reasons, suggesting maybe it was more about tracking advocates generally.

86

2: And this wasn't just happening right at the San Diego border.

87

1: Apparently not. The Boston Review mentions a report by Dana Francesca Haynes to the U.N. documenting 37 cases where immigration advocates and activists were stopped while traveling, sometimes far from the border, suggesting maybe broader watch lists were involved.

88

2: It feels like a pattern going back a bit, too.

89

1: The article reminds us, yeah, Jeff Sessions talking about, about dirty immigration lawyers in 2017, then ICE summoning attorney journalist Dan Kowalski in 2018 just for sharing a leaked memo. It suggests a certain friction between the administration and those challenging his policies.

90

2: And it wasn't just lawyers, but activist groups, too.

91

1: Right. Pueblos and Fronteras activists reported more secondary inspections, heavy questioning. Some of them were apparently in that leaked database, too.

92

2: The Boston Review also mentioned journalists facing similar issues.

93

1: Mm-hmm. Increased reports of journalists being hassled by CBP, denied entry to Mexico, intimidating searches, which obviously raises huge red flags about press freedom and protecting sources.

94

2: And the article ended on a note about technology, didn't it?

95

1: Yeah, a sort of broader concern about all this data collection and electronic monitoring at the border. While maybe some see it as better than walls, the article warns about the potential downsides for privacy and civil liberties down the road. Unintended consequences, you know.

96

2: OK, so let's try and pull this all together. We've talked about these. Allegations from the administration against immigration lawyers, unscrupulous behavior, threats of sanctions, and how lawyers see that as clear intimidation. Mm-hmm. Then the really strange case of the DHS email telling a U.S. citizen attorney to deport herself, highlighting potential system errors and, well, the fear that it causes.

97

1: Right, the macaroni incident.

98

2: Then the detention of attorney Amir Mockled at the airport, raising serious questions about targeting based on who he represents. Yeah.

99

1: The chilling effect concern.

100

2: And finally, placing all this within that broader context from the Boston Review, the leaked database, the reports of activists and journalists being harassed, suggesting a wider pattern.

101

1: It paints a picture based on these specific reports. Exactly.

102

2: And just to reiterate, we're bringing this information based on these sources. We're not endorsing any political viewpoint here, just laying out what's been reported. Absolutely.

103

1: Which leads us, I think, to a final point for people to chew on.

104

2: Go for it.

SPEAKER_01: Well, if you take all these reported incidents, what could the long-term impact be, you know, for things like due process, for the ability of vulnerable immigrants to even get legal help if lawyers feel targeted?

105

2: Yeah, that's a heavy question. And how does this kind of scrutiny, this reported harassment of lawyers, activists, journalists, how might that affect just advocacy and dissent more broadly in the country?

106

1: It really forces you to think about those fundamental constitutional questions, doesn't it? Yeah. About access to justice, freedom of speech. Yeah. About rich government oversight. Lots to consider based on what these reports are suggesting.