Migrate from Kayako to Zendesk

Kayako Conversations map 1:1 to Zendesk Tickets. We map Conversation status to Zendesk Ticket status, priority to priority, assignee (via email lookup against Zendesk User table) to assignee, and channel to the Zendesk channel field with the original requester metadata preserved. Message threads transfer as Ticket Comments. Any Conversation without a valid requester email is flagged for admin review before migration because Zendesk requires a requester on every imported ticket.

Kayako Agents and Admins map to Zendesk Agents by email match. Role and permissions from Kayako (admin, agent, team assignment) are documented for manual role assignment in Zendesk because Zendesk's role model uses a different permission hierarchy. Any Kayako Agent without a matching Zendesk account is placed in a reconciliation queue for the admin to provision before tickets are assigned.

Kayako Organizations map directly to Zendesk Organizations. The Organization domain becomes the Zendesk Organization domain field and is used as a deduplication key during import. We create Organizations before Users and Conversations so that the Organization lookup relationship is satisfied at the moment of User and Ticket insert.

Custom fields on Kayako Conversations require API field key discovery during scoping before any data moves. Each Kayako custom field maps to a Zendesk Custom Field of the matching type (text, dropdown, checkbox, date, numeric). Zendesk drop-down and multiselect fields automatically generate tags from selected values on import, which can duplicate existing tags if the source data uses both custom fields and manual tags for the same label. We document this behavior and recommend tag deduplication as a post-migration step.

Kayako Knowledge Base articles and their category hierarchy migrate to Zendesk Guide, which is a separate product that must be activated before import. We export articles and their category structure from Kayako, then rebuild the category hierarchy in Zendesk Guide sections and categories. Zendesk Guide Enterprise supports hierarchical article subsections up to five levels deep with a maximum of 20 subsections per parent section. Only the default language migrates unless the customer has multilingual content requiring manual section recreation in each locale.

Kayako Knowledge Base categories map to Zendesk Guide Sections. We preserve the parent-child hierarchy and reparent articles at the destination. Naming conflicts with existing Zendesk Guide sections are resolved by appending a suffix or by the customer choosing to merge during scoping.

Kayako Conversation tags migrate as Zendesk Tags applied to the corresponding Ticket. Tags are preserved as plain string labels and do not require special type mapping. Zendesk's tag model supports unlimited tags per ticket with no hierarchical structure. Tag readability and deduplication are handled post-migration if the source data has inconsistent tagging conventions.

Kayako SLA definitions (first response time, next response time, resolution time, business hours) are configuration objects that do not export via API in a directly portable format. We capture SLA metadata during discovery, map it to the equivalent Zendesk SLA Policy fields, and deliver a written SLA configuration guide for the admin to create the target SLA policies in Zendesk Admin. Each Kayako SLA tier maps to a Zendesk SLA Policy with matching time targets.

Conversation message attachments require separate API calls per Conversation, as Kayako does not bulk-export attachments. Files stored as inline images in message threads migrate as attachments linked to the parent Comment. Zendesk enforces plan-dependent file size limits (50MB on Suite Team, higher on Enterprise), and we flag any Kayako attachments exceeding the target plan's limit during scoping. After migration, we verify a representative sample of attachments to confirm they remain linked to the correct Ticket Comments.

Kayako automations (triggers, conditions, actions) are configuration objects with no portable API export. We do not migrate automations as code. We deliver a written inventory of every active Kayako automation rule covering trigger events, conditions, actions, and escalation logic, paired with a Zendesk Trigger and Macro equivalent reference. The customer's Zendesk admin rebuilds these post-migration, or a Zendesk implementation partner handles the rebuild as a separate engagement.