key is used. Detection systems running on the mail
servers of individual organizations or cloud service
providers cannot analyse encrypted mails, increas-
ing the probability of successful attacks. To examine
whether signatures and encryption can be misused for
phishing, we conducted two field studies investigat-
ing the mechanisms’ influence on the effectiveness of
phishing attacks.
The rest of the paper is organized as follows: Re-
lated approaches are described in Section 2, which
build the basis for our studies in Section 3. The out-
comes of our two field studies are described in Sec-
tion 4 and discussed in Section 5. Section 6 concludes
the paper and gives future directions.
2 RELATED WORK
Several researchers have published work on phish-
ing. We want to highlight phishing mediums and how
different factors impact the success of phishing at-
tempts. Phishing research has so far mainly focused
on webpages and was mostly conducted via user stud-
ies (Ferreira and Vieira-Marques, 2018). This may
be the case because websites are the most common
phishing medium, followed by email. Other means of
communication used for phishing are text messages
or phone calls (Yeboah-Boateng and Amanor, 2014),
social media like Facebook (Jagatic et al., 2007; Be-
nenson et al., 2017) and Twitter (Seymour and Tully,
2016), or recently QR codes (Vidas et al., 2013).
Signed emails can be embedded into anti-phishing ap-
proaches (Ren et al., 2007; Crain et al., 2010), but
to our knowledge no study targets signatures and en-
cryption as a means for phishers.
Recent related work researched the impact of var-
ious factors on the effectiveness of phishing attacks.
The factors can be categorised into user-based fac-
tors and the overall phishing setup. The follow-
ing related work describes the correlation between
demographic characteristics and phishing vulnerabil-
ity: (Sheng et al., 2010) and (Kumaraguru et al., 2009)
show that individuals between 18 and 25 years are
more vulnerable than older people. This result is con-
firmed by (Diaz et al., 2020), including only young
and mid-aged people. Another study extends the
scope of this research by including older people (Lin
et al., 2019). They observed a maximum vulnerability
to phishing in women over the age of 60 years. Fur-
ther studies (Sheng et al., 2010; Jagatic et al., 2007;
Halevi et al., 2015) confirm that women are overall
more vulnerable to phishing than men. Recent work
supports the thesis that computer-savvy people are
less vulnerable to phishing and that web skills cor-
relate to lower phishing susceptibility (Downs et al.,
2007). In a study at a university, researchers anal-
ysed how publicly available information in social net-
works can be misused for phishing attacks (Jagatic
et al., 2007). They observed that students from tech-
nology majors were the least vulnerable group. The
success rate for phishing attempts from an unknown
sender was as low as 0%, whereas it was up to 50%
for students from other departments. A comparable
result was found in (Diaz et al., 2020) during simu-
lated phishing attacks. Information technology and
engineering students had the lowest click rates in this
study. Low susceptibility was also related to frequent
interaction with computers and participation in com-
puter training. In contrast, (Alsharnouby et al., 2015)
found no correlation between technical competences
and the ability to identify phishing correctly. Unlike
computer experience, IT security experience is often
described as a factor that distorts the results of a study.
To eliminate this factor, knowledge in IT security was
an exclusion criterion in a set of phishing studies, e.g.
(Jakobsson et al., 2007) excluded students who at-
tended an IT security lecture and (Downs et al., 2006)
excluded subjects if their answers in a survey indi-
cated increased security awareness. The setup of the
phishing attack itself is pivotal for its effectiveness.
Targeted content raises the success rate of phishing
messages, but the effectiveness depends on the recip-
ient. A widespread spear-phishing experiment was
performed by (Williams et al., 2018). They observed
that people are more vulnerable at their workplace if
phishing messages use persuasion techniques such as
authority and urgency. The impact of different per-
suasion techniques in relation to the recipients’ de-
mography was explored by (Lin et al., 2019). They
determined that young adults are most responsive to
scarcity and older adults to reciprocation.
These observations support our assumption that
the effect of signatures and encryption depends on the
recipients and the email context. Therefore, computer
experience and security-related email content are fac-
tors considered in our studies.
3 STUDIES
This paper presents the results of studies on whether
signatures and encryption can be misused to increase
the effectiveness of phishing attacks. The relationship
is examined both in a security-related and in a social
context. Additionally, it is determined whether the
recipient being computer-savvy has an impact on the
effectiveness of encryption and signatures in phish-
ing emails. Two field studies with realistic OpenPGP
Field Studies on the Impact of Cryptographic Signatures and Encryption on Phishing Emails
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