I. Executive Summary: The Landscape of DSSC Deployment Pitfalls
1.1. Introduction to Deployment Complexity
The deployment of Delinea Secret Server Cloud (DSSC) represents a sophisticated integration effort, requiring seamless hybrid connectivity between the cloud tenant and various on-premises infrastructure components. The resulting architecture relies critically on the Distributed Engine (DE) for credential rotation and session management, and the Delinea Active Directory (AD) Connector for identity synchronization. Given this complex reliance on distributed components, failures during deployment are typically multi-layered, encompassing strict network segmentation, identity provisioning prerequisites, and highly sensitive application-layer configuration syntax. A comprehensive understanding of these failure modes is paramount for operational stability.
1.2. Foundational Failure Themes
Analysis of common deployment obstacles indicates that primary failures cluster around three critical areas. First, stringent firewall restrictions frequently disrupt the crucial communication paths, particularly those involving the DE's connection to the Azure Service Bus, necessitating precise port and IP allow-listing.1 Second, identity provisioning requires a specific two-step sequence involving administrator-initiated Group Sync and a user's initial Just-In-Time (JIT) login, leading to administrative confusion if prerequisites are incomplete.3 Third, the application layer, particularly for client access and Remote Password Changing (RPC), demands exact adherence to URL formatting and credential input syntax; even minor deviations trigger functional errors.4
1.3. Strategic Resolution Approach
Effective resolution of DSSC deployment issues mandates a structured, hierarchical troubleshooting approach. Initial efforts must focus on Configuration Syntax, ensuring precise adherence to application requirements (e.g., correct URL format, separate fields for machine name and username in RPC).4 If configuration is validated, the focus shifts to Permission Verification, particularly ensuring the domain-linked account has the required Secret Server and Delinea Platform administrative rights.3 Finally, thorough Network Connectivity checks must be performed, leveraging native Delinea diagnostics tools such as the Agent for Windows troubleshooting utility and the Secret Server Diagnostics console to verify DNS, firewall, and proxy integrity.7
II. Architecture and Foundational Network Connectivity Issues
This section addresses the physical and logical communication errors that frequently prevent the Distributed Engine (DE) and Delinea AD Connector from establishing and maintaining links between the on-premises environment and the Delinea Platform cloud tenant.
2.1. Distributed Engine (DE) and Proxy Configuration Errors
Issues related to outbound communication from the Distributed Engine are common in environments utilizing restrictive proxy servers or network inspection technologies. When troubleshooting these connectivity failures, general network tests are often insufficient. The primary step for diagnosis is enabling Debug Mode in the DE Log Files within Secret Server.8 This action provides the necessary low-level logging detail to capture granular failures during Layer 7 interactions, such as proxy authentication challenges, unexpected TLS interception issues, or subtle protocol negotiation failures that are not typically flagged by simple network monitoring.
Furthermore, identifying the exact source of outbound traffic is crucial. During initial diagnostics, administrators can view the IP address the distributed engine reports as being connected to the platform.8 This validation step ensures the DE is utilizing the expected network egress path, assisting network security teams in tracing the traffic through firewalls and proxies. For preliminary checks, the Agent for Windows hosts a powerful troubleshooting tool. Utilizing this tool to run the Delinea Identity Platform Connectivity Check verifies DNS resolution, firewall status, and proxy server settings directly from the DE host, quickly isolating external connectivity issues that prevent the engine from reaching the cloud tenant.7
2.2. Critical Firewall and Port Misconfigurations
The stability of the DSSC deployment relies entirely on meticulous firewall configuration, particularly concerning the Distributed Engine’s communication with the Azure Service Bus. By default, the DE establishes communication using Web Sockets over TCP/443.1 In environments where 443 traffic is heavily inspected or restricted, Delinea offers an alternative transport mechanism: AMQP, which necessitates opening specific, dedicated ports: TCP/5671 and TCP/5672.1 The choice between Web Sockets and AMQP represents an architectural decision based on the organization’s network security policy, balancing the ubiquity of 443 against the dedicated nature of the AMQP ports.
A significant point of failure involves the Web Application Firewall (WAF) communication. If outbound firewall rules are restrictive (i.e., configured for least privilege), IP allow-listing for the WAF is mandatory to ensure uninterrupted cloud connectivity.1 The environment leverages multiple regionalized cloud resources, meaning organizations must allow-list all provided public IP addresses (e.g., , , etc.) to prevent intermittent connectivity failures that occur when the DE attempts to connect to a different geographical entry point.1 Finally, if the DE is configured to act as an SSH proxy, TCP/22 must be open for inbound connections on the DE server to allow external clients to access internal SSH endpoints.1
The table below details the essential ports required for connectivity between the Delinea components and the wider network:
Delinea Connector and Distributed Engine Required Firewall Ports
2.3. Delinea AD Connector Communication Failures
The Delinea AD Connector, which bridges the cloud Platform with on-premises Active Directory directories, is highly sensitive to internal network filtering.9 While its outbound link to the Delinea Platform requires TCP/443, its critical dependency lies in its internal, unfiltered access to Domain Controllers (DCs).
The connector must be able to communicate with DCs across several standard, yet often restricted, ports for core identity functions. These required internal access paths include TCP/88 for Kerberos authentication, TCP/135 for Remote Procedure Call (RPC) endpoint mapping, TCP/389 for standard LDAP authentication queries, and TCP/3268 for Global Catalog access.9 If the host machine running the AD Connector is placed in a restrictive network zone, any filtering of these ports will immediately cause synchronization and authentication failures. The large number of required internal ports confirms that the AD Connector must be treated as a highly trusted component, requiring a dedicated, high-trust network path to Domain Controllers to ensure reliable identity operations and time synchronization (UDP 123).9
III. Identity and Access Management (IAM) Integration Challenges
Failures within identity integration commonly arise from synchronization timing issues, confusion over administrator role permissions, and hidden dependencies like licensing constraints.
3.1. Active Directory Synchronization and Provisioning Failures
A frequently reported issue is the inability of administrators to view Active Directory users or groups, which were previously configured in Secret Server, within the Delinea Platform's 'Access > Users' console.3 This failure is usually the result of incomplete provisioning steps rather than a fundamental integration failure.
Two critical prerequisites must be met to achieve full visibility and functionality. First, a Platform Administrator must explicitly utilize the Delinea AD Connector to perform the Group Sync function, linking the Secret Server Cloud AD groups.3 Second, individual Secret Server Cloud AD users must execute their first log-in to the platform. Delinea leverages a Just-In-Time (JIT) model for user provisioning; the user identity is not fully provisioned onto the platform until this initial authentication occurs.3
Administrators observing delays in group membership updates—where a user added to a synchronized Platform group does not appear in the corresponding Secret Server group immediately—should recognize this as a function of the background process interval.3 To expedite urgent access needs, the administrator can bypass the scheduled process by navigating to Settings > Platform integration > Groups tab and clicking the Sync Now button, forcing an immediate membership update.3
3.2. Initial Admin Role and Secret Visibility Mismatches
During the onboarding process, administrators often face unexpected secret visibility issues when logging in with the foundational cloudadmin account. It is crucial to understand that while logged in as cloudadmin, the user intentionally will not possess existing Secret Server administrative permissions and will therefore be unable to see existing secrets.3 This lack of visibility is expected behavior and does not signal a failed integration.
This architectural decision enforces a clear segregation of duties between the initial cloud tenant setup role (cloudadmin) and the subsequent operational privileged access role. The solution requires transitioning administrative control to a domain-linked account. To gain full administrative visibility and access to secrets from the Delinea Platform, the administrator must first set up Active Directory users and then explicitly assign Delinea Platform and Secret Server Admin permissions to their personal domain account.3
3.3. Persistent Login Issues and Licensing Constraints
When a user encounters persistent login failures despite verifying their username and password, the troubleshooting procedure must expand beyond simple credential validation. The resolution process is precisely defined in two steps.3
First, the platform administrator must verify that the user's account information is correct and matches the identity store. Second, if credentials prove accurate, the administrator must immediately check the licensing page (cloud subscription) within Secret Server for two potential hard stops: exhaustion of available user licenses or expired subscription dates.3 This workflow reveals that Delinea imposes a license capacity check as a hard authorization gate during the login sequence. If the system is out of licenses, it returns a generic login failure, effectively treating licensing depletion as a critical access denial rather than an explicit license error message, which mandates the administrator quickly pivot from credential checks to capacity management.
IV. Client and Endpoint Access Issues
Client-side issues often involve environment dependencies, strict application requirements for URL syntax, and proper handling of certificates in hybrid environments.
4.1. Mobile and Desktop Client Connection Failures
Troubleshooting client connectivity typically involves verifying foundational application configuration. If the Desktop Client fails to start or produces a generic "Login Failed" error despite using correct credentials, the issue may stem from environment drift on the endpoint. The prescribed resolution in such cases is often the uninstallation and re-installation of Java.4 This requirement indicates that certain legacy or specific desktop components rely heavily on a pristine, correctly configured Java environment, which is prone to corruption or conflicting updates on end-user machines.
Furthermore, all client applications, including mobile devices, rely on the availability of the application programming interface (API) layer. Therefore, administrators must ensure that Enable Webservices is explicitly set to "Yes" under Administration > Configuration. If webservices are disabled, client applications cannot establish the necessary programmatic connection to the Secret Server instance.4
4.2. Incorrect URL and SSL Certificate Handling
A common error in mobile and client application configuration is incorrect URL formatting. The URL used by the client application must precisely match the Secret Server instance address but must exclude the /Login.aspx path.4 For example, a web URL of https://secretserver/ss/Login.aspx must be input into the client application as https://secretserver/ss.4 Failure to adhere to this rigid syntax results in a communication routing error, as the client expects a specific API endpoint structure rather than the general web login page.
SSL certificate management presents another critical hurdle. When using SSL, the certificate deployed on the Internet Information Services (IIS) instance must be valid and trusted by the connecting device.4 For organizations operating in isolated or internal network environments without external Internet access, users will encounter HTTPS certificate validation errors. In this scenario, if the organization utilizes a self-signed or enterprise certificate, the mobile client application provides a capability to bypass the validation message and proceed to connect.4 While this bypass is a necessary mitigation for disconnected environments, the secure, long-term resolution requires the proper distribution of the enterprise root Certificate Authority (CA) via organizational tools (e.g., MDM or GPO) to ensure the internal certificate is automatically trusted by the mobile device.
4.3. Multi-Factor Authentication (MFA) Connectivity and Configuration
MFA functionality is intrinsically linked to the stability of the connection between the local endpoint (via the Agent for Windows) and the Delinea Identity Platform (Cloud). The troubleshooting tools for MFA are localized to the endpoint itself.
The Agent for Windows provides a dedicated diagnostics utility accessible from the system tray or the agent configuration panel.7 This tool executes several critical checks:
Delinea Identity Platform Connectivity Check: This test diagnoses the functional connection to the cloud tenant by specifically verifying DNS resolution, firewall status, and proxy server settings.7
MFA Configuration Check: This verifies that the local computer is properly configured for MFA and, if applicable, confirms compliance with any zone configurations defined in the Privileged Access Service Admin Portal.7
This localized approach acknowledges that the most frequent cause of MFA failure is an interruption of the critical cloud identity path due to DNS, proxy, or firewall configuration errors local to the endpoint, placing the responsibility for immediate connectivity verification on the agent host itself.
V. Privileged Operation Stability: Remote Password Changing (RPC) Failures
Automated secret rotation (Remote Password Changing or RPC) is a core component of DSSC functionality. Failures in this area typically point to misconfiguration within the secret itself or blocked network access to the target endpoint.
5.1. RPC Syntax Errors and Credential Formatting
RPC functionality depends entirely on the accuracy and format of the input data stored within the secret. A frequent, yet deceptive, error occurs when managing local Windows accounts: the error message "The user name cannot be found" may appear if the administrator incorrectly includes the machine name within the username field.5
The resolution is highly specific: for local accounts, the administrator must ensure only the username is entered in the username field, and the machine name is placed exclusively in the dedicated Machine field.5
This sensitivity to credential formatting is further complicated by the deceptive error, "Change password failed: Unknown. (ERROR_CANT_ACCESS_DOMAIN_INFO)".5 When dealing with local Windows accounts, this error is often misleading, as it frequently results from the machine not being found due to an incorrect syntax or name.5 This failure occurs because the underlying Windows API misinterprets the machine connection attempt as a failed domain lookup when the target is unreachable or improperly addressed. For Active Directory accounts, the same error may genuinely indicate that the account lacks the required permissions to perform the password reset or that the domain name is abbreviated or incorrect.5 Administrators must follow a strict troubleshooting hierarchy, always checking the secret syntax before moving to network connectivity checks.
5.2. RPC Target Connectivity Failures
Once the secret syntax is verified, connectivity issues must be addressed. Common failures stem from incorrect target identification, such as using an abbreviated machine name (e.g., comp3 instead of the FQDN comp3.yourdomain.com).5 To isolate DNS resolution problems from network path issues, administrators should attempt to replace the FQDN or machine name in the secret configuration with the target machine’s IP address.5 If the RPC succeeds with the IP address, the root cause is a failure in the organization’s DNS infrastructure.
The final element of failure is the firewall blocking the necessary communication ports between the Distributed Engine and the target machine.5 This includes dynamic RPC port ranges, specific management ports (like TCP/22 for SSH or TCP/3389 for RDP), and potentially SMB ports (TCP/445).5
In cases where rotation fails, administrators can generate granular debug information by manually providing input parameters and running the test in Secret Server (under Admin > Remote Password Changing). This step runs the full rotation command and provides console output, which is essential for determining if the issue lies in the data presented to the password changer.10
Common Remote Password Changing (RPC) Configuration Errors
VI. Data Management and System Diagnostics
This section covers the intricacies of migrating data and using Delinea’s native diagnostic suite for comprehensive system health monitoring and configuration management.
6.1. Bulk Secret and System Import Errors
Migrating secrets and system data requires strict adherence to positional formatting to avoid mass import failure. Secret Server's importation feature processes data in batches, and the underlying parser is non-adaptive, relying purely on the order of fields.11
For CSV or Excel bulk secret imports, the following are critical requirements:
Do not include a header line. The field names are determined solely by their order.11
The fields must adhere strictly to the template order (e.g., Secret Name, AccessKey, SecretKey, Username, SecretId, Trigger).11
Any deviation in sequence or the inclusion of a header line will result in data corruption or failed import, emphasizing the necessity of meticulous pre-processing of source data. Similarly, when importing systems and accounts in bulk, the CSV template requires that multiple accounts associated with the same system must be listed on separate lines, all referencing the identical system name.12
6.2. Configuration Setting Import Permission Denials
When importing configuration settings (such as security policies or two-factor settings) failure is often caused by insufficient administrative rights, even if the user possesses general administrator access. Delinea enforces a high level of functional segregation of duties, requiring specific permissions for modifying critical security components.6
Examples of required granular permissions include:
Updating Radius or Duo two-factor settings requires the Administer Configuration Two Factor permission.6
Modifying SAML settings requires the Administer Configuration SAML permission.6
Editing OpenID Connect settings requires the Administer OpenID Connect permission.6
This security policy ensures that a general administrative role cannot inadvertently or maliciously disable or misconfigure enterprise-wide authentication mechanisms. Furthermore, during SAML configuration imports, the error Identity Provider Id was not found in the database indicates that the Identity Provider ID in the import file was modified after export. The resolution for adding a new identity provider ID is to set the corresponding value in the import file to 0.6
6.3. Advanced Diagnostics and System Health Checks
The Diagnostics section, accessible via Settings > Diagnostics or Admin > Diagnostics, is the central hub for assessing the operational health and configuration status of the Secret Server Cloud environment.13 This tool is invaluable not only for troubleshooting but also for proactive environment management and auditing.
Key features include:
Specifications Tab: Provides a comprehensive breakdown of the operating environment, including OS configuration, Database Environment details (SQL version, connection string), Proxy Configuration, and key Secret Server environment parameters.13
Background Processes and Scheduled Jobs Tabs: These tabs allow administrators to monitor running tasks, verify thread identities, track last activity times, and identify failed scheduled jobs.13
Beyond monitoring, the Diagnostics section offers critical maintenance tools. Administrators can request a Clear Cache action 13 and, more importantly for resolving operational lags in synchronization or provisioning, click Recycle Background processes.13
The ability to export all application settings in CSV format and download the full diagnostics package (including Node and Engine logs) as a *.txt file 13 is fundamental for support workflow. This capability allows security managers to capture a complete system snapshot (OS config, DB status, and application settings) that can be compared against configuration baselines or provided to Delinea support, significantly reducing diagnosis time by preemptively identifying local environment misconfigurations.
VII. Conclusions and Strategic Recommendations for Operational Readiness
Based on the analysis of frequent deployment and operational pitfalls within Delinea Secret Server Cloud environments, stability hinges on pre-emptive architectural compliance and rigorous configuration management.
Mandatory Network Access Protocol Enforcement: Prior to any application-level configuration, organizations must finalize and implement the definitive network path for the Distributed Engine and the AD Connector. This involves explicitly allow-listing all required Azure Service Bus IP addresses due to regional dependence 1 and ensuring high-trust, unfiltered internal communication paths for the AD Connector to Domain Controllers across all necessary ports (TCP/88, TCP/135, TCP/389, TCP/3268).9 Failure to achieve this foundational network integrity guarantees intermittent service interruptions.
Formal Identity Transition and Delegation: Administrators must formalize the transition from the temporary cloudadmin role to a permanent, domain-linked administrative account. This process requires explicitly assigning both Secret Server and Delinea Platform administrative permissions to the operational domain identity.3 By treating cloudadmin purely as a bootstrapping identity, the organization maintains operational visibility and adheres to the designed segregation of duties, eliminating the "visibility gap" frequently encountered post-integration.
Strict Enforcement of RPC Data Syntax: To mitigate the risk of deceptive RPC failure messages—specifically the ERROR_CANT_ACCESS_DOMAIN_INFO error—the organization must standardize and enforce strict configuration policies for secret fields.5 This includes mandatory training to ensure local Windows accounts are configured with the machine name strictly separated into the dedicated Machine field, thereby preventing the underlying Windows APIs from misinterpreting local credentials as failed domain attempts.
Proactive Utilization of System Diagnostics: The Secret Server Diagnostics suite must be integrated into routine operational auditing. Administrators should use the Export diagnostics feature to regularly document and audit the environment's health, settings, and configuration parameters (Specifications, App settings).13 This practice allows for timely detection of configuration drift or resource exhaustion (e.g., DB or OS metrics) and provides immediate, comprehensive data required for efficient escalation to support when deep technical faults arise.
Works cited
Secret Server Cloud Customer Example Architectures - Delinea Platform, accessed October 7, 2025, https://docs.delinea.com/online-help/architecture/secret-server/secret-server-cloud/customer-examples/index.htm
Ports and IP Addresses Used by Secret Server - Delinea Platform, accessed October 7, 2025, https://docs.delinea.com/online-help/secret-server//networking/general/secret-server-ports/index.htm
Troubleshooting Onboarding Issues - Delinea Platform, accessed October 7, 2025, https://docs.delinea.com/online-help/delinea-platform/getting-started/onboard-troubleshooting.htm
Troubleshooting, accessed October 7, 2025, https://docs.delinea.com/online-help/secret-server-mobile/ts/index.htm
Remote Password Changing Errors, accessed October 7, 2025, https://docs.delinea.com/online-help/secret-server-11-6-x/remote-password-changing/rpc-errors/index.htm
Exporting and Importing Secret Server Settings, accessed October 7, 2025, https://docs.delinea.com/online-help/secret-server/admin/export-import-settings/index.htm
Troubleshooting Multi-Factor Authentication - Delinea Platform, accessed October 7, 2025, https://docs.delinea.com/online-help/server-suite/admin/mfa/troubleshooting.htm
Troubleshooting Proxies, accessed October 7, 2025, https://docs.delinea.com/online-help/connection-manager/ts/proxies.htm
Customer Firewall Requirements - Delinea Platform, accessed October 7, 2025, https://docs.delinea.com/online-help/delinea-platform/getting-started/firewall-requirements/index.htm
Troubleshooting Heartbeat and RPC Errors for Linux Secrets, accessed October 7, 2025, https://docs.delinea.com/online-help/secret-server-11-6-x/troubleshooting/troubleshooting-connection-errors-linux/index.htm
Importing Secrets, accessed October 7, 2025, https://docs.delinea.com/online-help/secret-server-11-6-x/secret-import-and-export/importing-secrets/index.htm
Importing Systems and Accounts, accessed October 7, 2025, https://docs.delinea.com/online-help/cloud-suite/resources-remote-clients/add-resources/import/index.htm
Diagnostics - Secret Server, accessed October 7, 2025, https://docs.delinea.com/online-help/secret-server/diagnostics/index.htm
No comments:
Post a Comment