Leading information security executives gathered at the 10th Annual Pratum Secure Iowa Conference during one of the breakout sessions to discuss the corporate and technical role of the Chief Information Security Officer (CISO) and the challenges of balancing risk management with nimble strategic information security decision-making.
The panel was asked by moderator David Cotton what first steps a new CISO should take in approaching security and business interests, and the panel was quick to point out that the advice is the same, whether a CISO is new to the role, whether the role itself is new or even if the CISO has been in the position for a long time: fostering a security culture is the key.
Anderson identified that corporate security policy was not mature when she first became a CISO, but even as company policies have matured, security culture does not necessarily follow suit. Thus, one of the objectives of any CISO should be to identify and foster a healthy security culture. That means speaking to the technical and business sides of the company. Making ongoing comprehensive discussions with both helps to identify pain points, opportunities for improvement, and clarifying questions regarding budget.
Johnson emphasized the need to read, understand and act on reports and audits, both ones that precede a new CISO and ones conducted under a CISO’s watch. Knowing how predecessors handled and addressed reports can not only give guidance for current results, but can also provide better understanding to the overall security culture at the company.
Schmitt believes strongly in a CISO building – or building on existing – business and client relationships. As a former product manager, Schmitt gained invaluable insights into the client experience. In his current role as a CISO in healthcare, he takes advantage of a clinical mentor – a person who serves as a bridge connecting him to the patients of the medical center. In order to become an organization’s trusted advisor on security issues, a CISO must first learn the business before making big splash technical changes. A good CISO will master controls, understanding vulnerabilities and operations, but in addition to that, must also be trusted in those areas, and the way to do that is through understanding the business.
There are a number of mistakes that can be made in Information Security, but there are also a lot of misconceptions that corporations have about security. According to Johnson, it is still not uncommon to find a deeply held belief that “security is security’s problem” in many organizations. He views the CISO as having a unique opportunity to humbly educate engineers and leadership. When an organization begins to understand that the security department should not be the only line of defense and that security begins at the cultural level, it – as an organization – can then be positioned to be active in its own defense and growth.
Anderson concurred. A common frustration the CISO faces is when the Security department or team as the computer police at an organization. “It is not about following Security’s rules so they can check a box. It is really about establishing a secure environment for the clients and employees to freely conduct business.”
Schmitt approached the problem from a philosophical angle. “If you can implement ‘guardrails over gates’ you can help your organization and its people go where they want to go with the protection of guardrails with less temptation to circumvent a lot of gates. “Technically this includes mastering the basics and implementing them consistently and not becoming distracted by chasing the latest “shiny object” to pre-empt innovations at the cost of ignoring fundamentals.
The balance between risk management and business growth is delicate, and according to the entire panel, has no perfect model or silver bullet. All three CISOs agreed: knowing the risks is key and weighing the probability of those risks (especially when they are measurable) needs to be deliberate, consistent, but also fast. As Anderson put it, it is a “continuous dynamic decision process.” Johnson emphasized hiring “great people that you can trust…and then trust them!” Schmitt drilled down into the measurables in some detail and emphasized the importance of trusting those measurements when performing trade-offs.
However, there is ample opportunity to take advantage of fostering a security culture in order to build the business as well. The CISO can engage leadership across departments, learn the business and simultaneously communicate technical opportunities in non-technical ways. Johnson put it this way: despite the technical aspect of security decision-making, there is still a lot of “what does our gut tell us? And how do we approach that experience?” By having trustworthy staff and good relationships across the security culture, the CISO can focus less on persuading for “buy-in” because the non-technical leadership already feels invested and connected. Anderson strongly recommends regularly connecting with leadership outside of security, and communicating wins, losses and opportunities in a non-technical way. She also believes that the security team – not just security leadership – needs to know where the business is going. “From a security team point of view, where is the business going?,” she said, “How does that impact the team today? How do we resource those initiatives?” Then, it is the CISO’s job to ensure that the alignment with business goes all the way up through the hierarchy of the organization. Don’t assume the organization knows what security is doing it and why. Tell them.
The panel of CISOs found worthwhile certifications to be those credentials that symbolized passion, interest and curiosity, but saw little value in pursuing a certification unless an employer required it. In fact, one CISO held no certifications, one held many, and yet another had a few. They all said that the far more important attribute of a good CISO was adaptability and an undying curiosity. In fact, Johnson mentioned that it was possible to be overcertified to such a degree that he might question whether or not you even had the time to exercise practical skills in a CISO capacity. A passion-based approach might be better. “Certification can show that you have a desire to be in this space,” he said.
Schmitt said that certifications are useful as long as you actually have an interest in the certified subject, but that the key is to be engaged in the security community, to participate in tabletop exercises and capture-the-flag-style events, and to be an evangelist for security culture. For the CISO who really wants to target a high-value certification, Anderson recommends cloud security certifications, as there is currently a high and growing demand for cloud security expertise, and a certification can distinguish candidates.
As the session wrapped up, David asked the panelists to share any last words of wisdom for the working or aspiring CISO:
Schmitt: “Is your team moving the needle and if they are, are they getting positive feedback every day? Make small improvements every day, and ask yourself, are you better every day, just a little bit? And do you know how you measure that?”
Anderson: “Back in 2008, it [Information Security expertise] wasn’t daily news. Today it is. Cybersecurity opens the door. Don’t ask to be invited. Meet with leadership.”
Johnson: “Fundamentals – a business should invest in talent – basic controls, MFA, patching, security should matter when you are buying products of course but what is critical is that you hire trusted advisors.”
Meg Anderson of Principal Financial has been with the company for 35 years. She began her career in the Insurance Division as a COBOL programmer and advanced through the corporate ranks to lead a variety of network architecture, SASS, data warehouse and other data leadership roles. In 2008, she took the opportunity to become Principal’s CISO, a move she described to be at the time – technically – a “lateral move.” Driven more by career growth and an interest in learning more about infrastructure than in promotion, she found the new role – which she initially believed would be a relatively short-lived one for her – to be ideally suited to her natural curiosity, technical expertise and interest in fostering culture.
James Johnson’s background as IT manager at Pella Windows, pen tester, engineer and CISO at Honeywell provided the path for him to become global CISO at John Deere.
Ben Schmitt, CISO for Mary Greeley Medical Center has recently ascended to his position with a diverse background in product management, telecommunications and forensics at TDS Telecom, Danfoss and Dwolla, all of which he believes contributes to his “client-centered” approach to his duties at CISO.
Microsoft continues to up its game, and it’s critical for you to review, configure and tune the appropriate settings within Microsoft 365’s various services to ensure that you’re meeting proper risk tolerance levels.
Microsoft leverages a defense-in-depth approach in an effort to adhere to operational best practices to provide physical, logical, and data layer protections. These layers help to protect all 365 users, but every organization must ensure that their implementation and configuration of their tenant are configured securely.
Pratum highly recommends that you review the following guide and implement its ideas as needed. Remember: These defaults impact new mailboxes. Audit settings should be reviewed for any accounts created prior to January 2019.
Every Office 365 cybersecurity strategy should include extended detection and response (XDR) tools. These next-generation systems combine machine learning and rules created by analysts to monitor suspicious activity across your entire system, including Office 365 elements such as inboxes and software delivered through the cloud. Visit this page for an overview of managed XDR.
Pratum highly recommends the use of multi-factor authentication. User accounts are compromised daily resulting in the increased risk to losing control of key data and information. Business email compromise and credential harvesting attacks are a constant threat to an organization. One of the best security defenses to thwart this loss is requiring users to use multi-factor authentication (MFA) to access key systems, such as email and file sharing. MFA can significantly decrease the success of an attacker tactics even when they compromise the user’s password, as they would also need to compromise the additional factor. These additional factors can be in many forms, such as a hard token or an application on a smart device. There exist multiple methods and solutions for multi-factor authentication for Microsoft 365, and the configuration options will vary depending on licensing. Azure, Intune, and Enterprise Mobile Device Management plans offer additional capabilities when deploying or enforcing this security feature.
Administrators can review and enforce additional restrictions or relax certain policies such as multi-factor authentication requirements when users are accessing resources from a trusted location or compliant device. These scenarios increase the likelihood the user accessing the resource is trusted and therefore decrease the security requirements needed to authorize the user. This feature works very well to find the right balance between security and convenience. Furthermore, restricting access from locations and devices that employees should never be logging in from can also be enforced and alerted against. An Azure AD Premium license is required for use of conditional access policies.
Phishing causes a considerable share of all breaches and cyber incidents within organizations, especially those with Microsoft 365. Forensic analysis typically reveals the culprit is an e-mail that posed as a shared document hosted in a domain that looks remarkably like OneDrive. When the user clicks the link, they arrive at a sign-in page that mirrors Microsoft’s 365 login page. Unfortunately, the credentials entered within this fake screen go straight to the attacker, who may then have complete access to the user’s e-mails and files. That’s what makes multifactor authentication (MFA) one of the most successful ways of preventing an attacker from gaining access even after they have compromised a password.
It’s also critical that you recognize when a password has been compromised. It becomes even more important if the attacker successfully authenticates to the victim's data. This information is key to investigating what activity was performed or determining whether it triggers breach notification requirements.
To ensure you have sufficient data to detect these threats or perform a proper investigation, you must ensure your Microsoft 365 tenant is auditing all the crucial areas. In January 2019, Microsoft recognized the need for this information and enabled it with respect to mailbox auditing.
Reference: Manage Mailbox Auditing
Event data containing critical information; such as user and system activity, changes, authentication details, etc.; is extremely important to have captured log data to detect threats, especially when performing an investigation. An administrator must manually enable the “Office 365 audit log search.” This feature may record user and admin activity for 90 days; however, it is best to validate which retention settings are configured based on licensing/configuration. This data can typically and should be piped to a security information and event management (SIEM)/XDR Solution for additional monitoring and correlation. Note that only mailbox audit events for E5 users are available in the audit log searches within the Security & Compliance Center or through the Office 365 Management Activity API.
Reference: Enabling Audit Logging
In Office 365, administrators should enable mailbox audit logging to record mailbox access activity. By default, mailbox auditing is disabled. If a security incident occurs, there may be very little data if any regarding an attacker’s activity. However, once audit logging is enabled, the audit log can be searched for mailbox activity. Additionally, when mailbox audit logging is turned on, some actions performed by administrators, delegates, and owners are logged by default. It is recommended to enable at a minimum the default logs as well as the referenced commands below; however, each organization should determine what logging level is needed.
We highly recommend enabling the ‘UpdateInboxRules’ setting for all types of users. Attackers commonly set up a forwarding rule that forwards a copy of the user's inbox to a second address such as a Gmail account. This provides them persistent access to the user’s e-mail even after they update their password! We recommend auditing and reviewing these rules. Be prepared to add logic to filter out legitimate, employee-created forwarding rules. We recommend using logic that looks for forwarding rules that are redirecting e-mail outside of the organization or tenant domain. Even if an employee is attempting to forward e-mail to their personal mailbox, this is a bad practice, as the data is no longer controlled or protected by company policies.
Mobile device management (MDM) should be reviewed and understood by each organization. Ensuring the proper policies are defined and agreements are in place for employees of the business. Exchange Administration can be configured to define policies on which devices/users can communicate with the email servers. Policies to enforce compliance to company policies such as device encryption should be enabled as well as which devices can connect. For additional features and control, plans can be purchased for Microsoft Intune and/or Enterprise Mobility Security.
Reference: MDM for Office 365 versus Microsoft Intune
Users that are communicating via email, and have a E3 or higher license, can leverage Office 365’s Message Encryption feature. An administrator can also define a mail flow rule to encrypt email messages that contain a keyword in the subject. Encryption with Rights Protection can be leveraged to reduce the ability for users that receive encrypted messages to forward them to unintended recipients, print, or access them within certain time restrictions.
Reference: Define a Mail Flow Rule to Encrypt Email
A rule can be created via Exchange Admin Center to set the spam confidence level (SCL) to ‘9’ if the messages sender’s address domain belongs to any of the organizations valid domains and the message is received from ‘Outside the organization.’ A spoofing filter rule definition will help limit the amount of phishing emails that are delivered.
A very popular vector for malicious actors is spoofing a company’s executives or high trust individuals. The actor will spoof accounts such as the CEO, HR or IT leader asking staff to perform actions that can lead to a breach or loss. Examples of this are as simple as asking to purchase gift cards, login to a web site to approve something or providing private company information. For organizations that have Microsoft 365 Defender you can easily remedy this vector. Microsoft 365 Defender has additional Anti-phishing capabilities that can protect organizations from impersonation. Microsoft 365 Defender also protects your domains from spoofing in a much better way that the old method of transport rules.
Licensing requirements: Microsoft 365 Defender prerequisites
Implementing DMARC (Domain-based Message Authentication, Reporting and Conformance) with SPF (Sender Policy Framework) and DKIM (DomainKeys Identified Mail) is recommended for all organizations. These features provide an additional layer of protection against spoofing and phishing emails. They can also help to reduce the risk of business email compromise attacks. DMARC settings will tell the Exchange servers what to do with messages that were transmitted with the organization’s domain that fail SPF or DKIM validation checks.
A DMARC TXT Record also helps to prevent spoofing and phishing attacks by verifying the IP address of an email's author against the alleged owner of the sending domain. The DMARC TXT record identifies authorized outbound email servers. The destination email server can validate the message that originated from the authorized outbound email servers.
An SPF record is used to define IP’s that are authorized to transmit email for a given domain. This way, if an attacker spoofs the organizations domain from an IP address not on the list it can fail delivery to the recipient automatically.
DKIM should be configured once the SPF and DMARC records have bene created. DKIM adds a digital signature to each email message’s header information. It is highly recommended the DMARC settings are reviewed and deployed with careful consideration such not to disrupt intended mail flow.
Reference: Define DMARC to Validate Email
After DMARC is configured for an organization a rule should be created in the Exchange Admin Center to direct where mail that fails the DMARC validation is directed. A definition can be created such as ‘Deliver the message to the hosted quarantine’ if ‘authentication-results’ header contains “dmarc=fail” and sender’s address domain portion belongs to any of the organizations valid domains and the message is received from ‘Outside the organization.’ Under Additional properties the Sender address matches should be set to Header.
Business email compromise can result in attackers configuring mailbox forwarding rules to send a copy of email outside of the organization to a 3rd party email domain. Employees may also desire to send copies of emails to personal email accounts. These forwards reduce the overall security of the organization. A rule can be created in the Exchange Admin Center to reject any messages and include an explanation that client forwarding rules to external domains are not permitted. This rule can be defined if a message is sent ‘outside the organization’ and the message type is ‘auto-forward’ and the email is received from ‘inside the organization.’ It may also be beneficial to configure alert definitions based on these conditions to ensure an account was not compromised. An alert definition can be defined while creating the rule to email a notification to the defined contact upon triggering.
Enabling the safe list of IP addresses that are permitted for each respective domain can help to reduce trusted senders from getting blocked.
Reference: Connection Filters
Configuring alert policies can help track user and administrator activities, malware threats, and data loss incidents within each organization. Alerts should be defined for malware incidents, email forwarding/redirect rules, anomaly detection, and suspicious activity at a minimum. It is highly recommended event data is also transmitted to a SIEM solution for correlation and long-term event storage. If a traditional SIEM is not being leveraged, consider Microsoft's Cloud Native SIEM, Sentinel. They allow for free logging of many Microsoft 365 events for 30 and even 90 days in certain scenarios. Additional fees may apply and typically include data storage within log analytics or any custom event sources. Consider a managed service provider such as Pratum to assist with a fully managed environment.
Microsoft Secure Score will help analyze each organizations Office 365 security based on administrative activities as well as audit security settings and make recommendations. A score is then provided based on the settings and is re-evaluated in an on-going basis. Secure score is a fantastic tool that will help you understand and evaluate how you are offsetting risk by leveraging the various security features across 365. It is highly recommended all of the results are evaluated and considered for your organization. *Note: Settings should be carefully reviewed and exceptions may need to be made to not disrupt mail flow for legitimate emails which are being spoofed intentionally. The Secure Score feature is being heavily supported and being rolled out across multiple areas of the Microsoft 365 cloud. This scoring feature should be reviewed on a reoccurring basis as it provides a valuable amount of data and is becoming more sophisticated with each release.
Reference: Secure Score Overview
There exists a multitude of features highlighted below within Microsoft 365 that should be reviewed and configured with appropriate settings. These features should each be used in accordance to the business’s IT Security requirements, the following should also be considered/configured within the Security and Compliance section.
Data Loss Prevention – Policy protection to assist with identifying and protecting sensitive data.
Data Governance – Assists with classifying content, defining retention rules and data destruction.
Classifications – Labels can be applied to email or documents to enforce policies such as retention settings or sensitivity.
Data Privacy – GDPR requirements and access to their personal data.
Threat Management – Threat tracking and attack simulators can be performed to assess risk.
Customer lockbox requests allow organizations to control how a Microsoft support engineer accesses company data when necessary to do so. It is available through the E5 plan or with the advanced compliance license. This feature should be enabled if available.
Reference: Enable Customer Lockbox
Opening the aperture from looking just at email, Microsoft offers an expansive set of tools to protect organizations. Having a well-integrated security program will create efficiencies and help keep the organization up to date with today’s modern threats. Organizations should evaluate their current licensing with Microsoft and make sure they are leveraging everything they have. They should also look at the benefits of adjusting it by either stepping up or adding individual licenses to improve their security posture. Implementing tools like Microsoft Defender for Office 365 has features like safe links that can protect emails from malicious links by rewriting them and using AI to test them prior to the end user receiving the message. Microsoft has the tools available to give administrators insights into malicious emails and office attachments.
Reference: Microsoft 365 Defender
Reference: Microsoft Defender for Office 365
Reference: Microsoft Defender for Cloud
Reference: Microsoft Sentinel
Microsoft has millions of users leveraging Microsoft Office 365 with expectations of over two thirds of its business customers being in the cloud by 2019. Microsoft leverages a defense-in-depth approach in effort to adhere to operational best practices to provide physical, logical, and data layer protections. These layers help to protect all individuals that leverage 365, however, it is the responsibility of each organization that uses 365 ensure their implementation and configuration of their tenant is also configured securely. Each business has the responsibility to review, configure and tune the appropriate settings within the various areas of Microsoft 365’s services to ensure proper risk tolerance levels are met.
For assistance with evaluating your organizations risk or cyber security needs, please contact Pratum.Editor's Note: This post was originally published in July 2018 then updated in November 2020 and has again been updated for accuracy and comprehensiveness.
If your cyber insurance premium blew up this year, you’re not alone. Cyber insurance rates have increased 110% in the U.S. for the first quarter of 2022 according to Marsh's Global Insurance Market Index. And to make the situation even more frustrating, the application process has become extremely complex as insurance companies ask hundreds of questions at renewal time.
In this post, we’ll describe the key ways you can get lower cyber insurance premiums and survive endless underwriting questionnaires while still getting the coverage essential to your business.
The following policies and tools have the dual benefit of making you more secure and convincing underwriters that you’re a lower risk. Ross Ingersoll, an executive risk & cyber account executive at one of Pratum’s insurance-industry partners, Holmes Murphy, in Des Moines, Iowa, points to three security policies/tools every insurance carrier wants to see.
“MFA is, by far, the leading indicator to prevent ransomware losses, and it’s the number one thing carriers are looking for,” Ingersoll says. Without a sound MFA policy, you may be denied coverage. And a general answer of “yes, we have MFA” won’t satisfy most carriers. They want details on how your MFA policy protects admin level users, secures all remote access and secures corporate email on non-corporate devices and web apps.
Ransomware struggles to get past these systems that can catch threats early and shut them down. An IBM study found that organizations using security AI and automation spend 80% less handling a breach. A solution like Pratum’s Managed XDR can detect anomalous activity, correlate actions into a threat picture and proactively shut down attacks. And that often happens in milliseconds.
Ingersoll asks his clients: “Do you have an offline or segregated backup solution? Have you tested it frequently? Monthly? Quarterly? Is access to the backup restricted by MFA? Along with that, do you have an incident response plan to access the backup and have you tested the IR plan?”
The last couple of years have rocked the cyber insurance landscape with three factors hitting almost simultaneously. Insurance companies had set rates artificially low because they lacked enough history to do accurate underwriting. Then the ransomware wave and remote workforces arrived simultaneously, sending claims skyrocketing.
Put all that together, and you get an industry trying to right-size its revenue in a hurry by jacking up rates. At the same time, cyber insurance companies have taken other steps to control their losses:
You probably can’t avoid a price hike. But your actions can lead directly to lower cyber insurance rates. Consider the following story from Ingersoll of Holmes Murphy:
Ingersoll recently met with a client six months before their cyber insurance policy was up for renewal. The client lacked several of the key security tools described below, but on Ingersoll’s advice, they quickly ramped up their security posture.
To measure the ROI, Ingersoll got insurance quotes before the improvements and after. With no security adjustments, the $3 million policy’s price would have jumped from $20,000/year to $80,000/year. And ransomware incidents would have been limited to $100,000 of coverage.
With the new security policies/tools in place, the client kept their original coverage amounts and saw the price rise to $35,000. That’s still a 75% increase—but it’s a lot better than paying 300% more for less coverage.
“The increase may be inevitable,” Ingersoll says. “But you can manage the increase while maintaining a robust policy. That’s the moral of that situation.”
Along with focusing on the key areas mentioned, you should brace for a significant time investment at policy renewal time. For both new policies and renewals, expect a long list of questions probing deeply into your information security policies and tools. We recently helped a client respond to 275 individual questions from their cyber insurance carrier.
So start 5-6 months before the renewal is due and get help from third-party experts such as Pratum and an experienced insurance broker.
Expect questions like these:
Pratum’s consultants help organizations create customized security plans that not only help with cyber insurance costs but secure the organization’s future. Contact us today for a conversation about how we can help boost your security posture.
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