To B or not to B: That ESTA Question
The US Visa Waiver Program isn't what it used to be. Since the implementation of the ‘‘Visa Waiver Program Improvement and Terrorist Travel Prevention Act of 2015 (passed in December), the US Government has signaled a preference for visa-based travel over visa-free travel in the name of security. This should come as no surprise.
Originally created as a travel program for low risk travelers to avoid having to apply for a B-1 (business) or B-2 (tourist) visa to enter the US, the Visa Waiver Program (VWP)has been transformed in the post-9/11 world into a "security partnership," to enhance monitoring of individuals entering the US.
Have you ever been arrested?
Visitors to the US became familiar with the I-94W -- the green card with questions about past transgressions (not to be confused with the Green Card identity document which, at the time, was pink). The form, completed upon arrival in the US, asked seven questions, ranging from drug addiction and terrorist/ Nazi membership to arrests for "crimes involving moral turpitude."
Acknowledging the electronic age and the utility of data collection for security purposes, US Customs and Border Protection (CBP), on instructions from the US Congress, created ESTA, the Electronic System for Travel Authorization. ESTA offered a means of preclearance prior to travel, but the terminology remained the same and that was problematic.
"Moral turpitude" is particularly problematic and has been deemed a "notoriously plastic" term by a US Federal Circuit Court. Whether groggy from a long flight, confused by the curious language, or simply indifferent, a lot of people became accustomed to perfunctory completion of the I-94W and, perhaps out of habit, did the same with ESTA.
In November 2014, CBP changed ESTA to remove the plastic terminology and replace it with definitive language: "Have you ever been arrested or convicted for a crime that resulted in serious damage to property, or serious harm to another person or government authority?"
That clears things up. Not. How does one define "serious?" Is shoplifting a KitKat bar serious damage to property or harm to another person? One would think not, but it is a CIMT. Is tax evasion harm to government authority? Perhaps, but regulatory violations would not normally be considered a CIMT.
Are you currently seeking employment in the United States?
Blurring the lines between legitimate business travel (attending meetings, conferences, and negotiating contracts) and actually working in the US (i.e. doing a job that could be done on the US economy) further complicates VWP travel. In the digital age, when much work can be done anywhere there is a reliable broadband connection, this restriction seems antiquated, but failing to identify when activity would require employment visa can have serious consequences.
Are you a citizen of any other country?
The Terrorist Travel Prevention and Visa Waiver Program Reform provisions of the Omnibus Appropriations legislation of December 16, 2015 (also known as ‘‘Visa Waiver Program Improvement and Terrorist Travel Prevention Act of 2015, or VWPITTPA’’) excludes from the VWP dual nationals of VWP countries and "countries of concern" (specifically Iraq and Syria, as well as Iran, and Sudan), or anyone who has travelled to any of the countries of concern since March 1, 2011 (with exceptions for certain official travel). The implementation of this provision began on 21 January with notifications of the termination of ESTA authorization being emailed to identified dual nationals. On 18 February 2016, the Department of Homeland Security added Libya, Somalia, and Yemen to the list of countries of concern, but only with regard to individuals who had travelled to those countries since March 1, 2011.
A brief survey of nationality law in "Countries of Concern"
Iran. Iranian law does not recognize dual citizenship; however, acquisition of another nationality does not automatically revoke Iranian citizenship unless such action is specified in the acquisition of the new nationality. The US State Department has stated that it considers dual US-Iranian citizens to maintain their Iranian citizenship, unless specifically revoked according to the laws of Iran. To abandon Iranian citizenship, an Iranian national must meet the following criteria: age 25 or above; consent from the Council of Ministers; transfer of all claims to Iranian property to an Iranian national. 
Iraq. Prior to the ousting of Saddam Hussein, Iraqi law specifically provided that the acquisition of citizenship in another country effectively renounced Iraqi citizenship, but that law was replaced in 2006 by legislation reinstating citizenship to those who had lost it. Dual nationals may still renounce Iraqi citizenship if they declare in writing the renunciation of their Iraqi nationality.
Sudan. The law of the Republic of Sudan provides for the termination of citizenship in the following situations: a declaration of renunciation; joining the service of another country where such action has been deemed a criminal offence in Sudan; acquiring de facto or de jure citizenship of South Sudan; and if, as a minor, one's responsible parent lost Sudanese citizenship. 
Syria. Syria's nationality law broadly recognizes continuation of Syrian citizenship for dual citizens unless affirmative steps are taken to renounce and even offers reclamation of lost Syrian nationality; however, there are certain actions which will trigger automatic loss of Syrian citizenship, such as joining a foreign military without prior authorization from the Syrian Minister of Defence or engaging in activity or work (or illicitly leaving Syria to enter) a country which is in a state of war with Syria--i.e. Israel).
How to answer those ESTA questions
I encounter a lot of would-be travellers to the US who struggle with how to answer the ESTA questions because of an historic arrest or brush with the law, which often resulted in nothing more than a warning or a caution. The question presented is typically framed as: either "How do I answer the question?" or "What if I say 'No?'" My first response is always: "Tell the truth," to the former, but I also like to provide some context for the latter.
This raises two issues: 1. Are you inadmissible under INA§212(a)(2)(A); and 2. would failure to disclose constitute a wilful misrepresentation of material fact under INA§212(a)(6)(C)?
Analysis of the first informs the second. If an historic transgression would render an individual inadmissible, the knowing failure to disclose that would constitute a wilful misrepresentation of material fact.
Life is not always so simple. Many people are not entirely sure they have been arrested (normally, I suggest that, if someone was fingerprinted by the police, they were probably arrested). Then, there is the Rehabilitation of Offenders Act, which absolves an individual of having to disclose minor historic issues. The ROA has no impact on US visas. Of course, the mere fact of an historic arrest may not mean the individual is inadmissible. Exoneration would, of course, excuse any arrest. Prior to 2014, a police caution or lesser sanction would not have any impact on visa eligibility; however, as a result of a change in policy in January 2014, cautions issued after June 2008 are considered to constitute "official confessions" which can be the basis for an inadmissibility determination.
Questions about citizenship and travel history should be more straight forward-- presumably, you would know if you are a dual citizen of or if you travelled to one of the named countries of concern in the past 5 years, but whether one is a citizen of another country may be unclear: What if you were born in Syria, but fled to Israel? Or Sudanese and accepted nationality in South Sudan? What if your family immigrated from Iraq to the UK 20 years ago and you haven't held an Iraqi passport since you left? One could easily think s/he had given up citizenship in a Country of Concern, only to learn s/he hadn't.
Momentary memory lapses and misrepresentation
The "I didn't understand the question" rationale for improper ESTA responses doesn't work as well as it did with the I-94W (and it didn't work so well then, either). If you didn't understand, you should have asked, is the standard attitude of consular and immigration officials. But a mistake need not necessarily result in inadmissibility.
This brings us back to that second issue: was the failure to disclose a wilful misrepresentation of a material fact made to obtain a US immigration benefit?
To be wilful, a misrepresentation must be made with knowledge of its falsity. To be material, the fact misrepresented must be substantive and related to a ground of inadmissibility. Knowingly failing to disclose a conviction for drug smuggling would clearly constitute a misrepresentation of a material fact because drug smuggling is an offence that would make an individual inadmissible. Failing to disclose dual nationality should not. Like other requirements of VWP eligibility, such as having a return ticket and maintaining nonimmigrant intent, an individual may be denied admission for not having an appropriate visa, but s/he should not be deemed to be inadmissible under INA§212(a)(6)(C).
How would an immigration inspector or consular officer know about a misrepresentation? Certainly, for something like an arrest history, that would become apparent in the course of applying for an immigrant visa, where presentation of a police certificate is required. For the casual traveller, however, increased monitoring of social media by US officials may also yield a treasure trove of information.
When in doubt, it's better to B than not to B
It may sound like a marketing ploy for a US immigration lawyer to advise people to apply for a visa, but don't just take my word for it. Use the Visa Wizard at https://travel.state.gov/content/travel/en/us-visas/visa-information-resources/wizard.html. While having a B-1 or B-2 visa in your passport won't necessarily guarantee entry to the US, it at least shows that a Consular Officer has reviewed eligibility and admissibility. And there are benefits: B visa holders can enter the US for up to 6 months, rather than 3 on the VWP; and can change visa status while in the US (which is not possible on the VWP).
 INA §217
 Secure Travel and Counterterrorism Partnership Act of 2007.
 Ali v. Mukasey 521 F.3d 737 (7th Cir. 2008)
 See 9 FAM 302.3 (Unavailable) formerly 9 FAM 40.21(a)N2.3-2
 H.R.158 - 114th Congress (2015-2016)
 See Written testimony of CBP Commissioner R. Gil Kerlikowske for a House Committee on Homeland Security hearing titled “National Security and Law Enforcement: Breaking the New Visa Waiver Law to Appease Iran,” reprinted as News: CBP Commissioner Written Testimony for the House Committee on Homeland Security available at http://discuss.ilw.com/showthread.ph...eland-Security [accessed 16 February 2016]
 DHS Announces Further Travel Restrictions for the Visa Waiver Program. Available at https://www.dhs.gov/news/2016/02/18/dhs-announces-further-travel-restrictions-visa-waiver-program [accessed 19 February 2016]
 See Canada: Immigration and Refugee Board of Canada, Iran: Whether an Iranian woman loses her Iranian nationality if she marries a non-Iranian, or acquires another nationality without informing Iranian authorities; whether a child born to an Iranian mother and a non-Iranian father is entitled to Iranian citizenship, 1 May 1999, IRN31882.E, available at: http://www.refworld.org/docid/3ae6ad9423.html [accessed 13 February 2016]
 Iraqi Nationality Law [Iraq], Law 26 of 2006, 7 March 2006, available at: http://www.refworld.org/docid/4b1e364c2.html [accessed 13 February 2016]
 United Kingdom: Home Office, Country of Origin Information Report - Sudan, 11 September 2012, available at: http://www.refworld.org/docid/505192fe2.html [accessed 13 February 2016]
 Legislative Decree 276 - Nationality Law [Syrian Arab Republic], Legislative Decree 276, 24 November 1969, available at: http://www.refworld.org/docid/4d81e7b12.html[accessed 16 February 2016]
 Matter of G-G-, 7 I&N Dec. 161 (BIA 1956).
 See 9 FAM 302.9-4(B)(5)
 “U.S. to Further Scour Social Media Use of Visa and Asylum Seekers,” NY Times, 23 February 2016, available at http://www.nytimes.com/2016/02/24/us/politics/homeland-security-social-media-refugees.html?mwrsm=LinkedIn&_r=0 [accessed 24 February 2016]
Reprinted with permission.
About The Author
Steven D. Heller is Managing Director of Heller Immigration Law, Ltd. in Lewes, East Sussex, UK. A member of the New York Bar and the American Immigration Lawyers Association, he has appeared on CNN as an expert in US immigration and visa matters and has written for various publications, and is coauthor of US Citizenship for Dummies. On the web: www.us-visa.co.uk. email: email@example.com