A Kayako to Zendesk migration requires the &archived=1 API parameter to avoid silently losing closed tickets. Use Zendesk's Ticket Import API, not the standard Tickets API. Expect 1–3 weeks DIY or 3–5 days managed.
Step-by-step guide to migrating from Kayako to Zendesk. Covers API extraction, the archived ticket trap, object mapping, rate limits, and ETL process.
Read this first
Pair-specific gotchas that catch teams out. Each one has cost somebody a weekend.
Quick Answer
This is a moderately complex migration. The single biggest risk is silently losing archived tickets — Kayako's default API endpoint omits cases closed more than 30 days ago unless you append &archived=1. Kayako Macros, SLAs, Triggers, Automations, and Views cannot be migrated programmatically and must be rebuilt manually in Zendesk. Expect 1–3 weeks of engineering work for a DIY approach, or 3–5 business days with a managed service. Teams with fewer than 10K tickets and no custom fields can run this in-house. Teams with 100K+ tickets, attachments, and custom field mappings should use a managed migration service.
If you start with Kayako conversations instead of cases, or you forget archived=1, you
If you start with Kayako conversations instead of cases, or you forget archived=1, you can finish the project with a clean-looking Zendesk instance and still be missing years of historical support data.
Kayako's total_count can shift between pages if cases are created or updated during extraction
Treat any API export as a point-in-time snapshot and run a delta sync before cutover.
If your source has very long tickets, create one imported ticket with the historical
If your source has very long tickets, create one imported ticket with the historical thread baked into ordered comments. Do not create the ticket and then update it hundreds of times — Zendesk limits updates to 30 per 10 minutes per user per ticket.
The runbook
Work top to bottom. Tick steps as you go — your progress is saved in this browser.
01 Discovery Establish why you are moving, what "done" means, and who signs off.
Objective A written scope with agreed success criteria, a named owner per workstream, and a budget approved by finance.
Keep these open
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Pull the real numbers out of Kayako
Export counts for tickets (open and closed separately), contacts, organisations, attachments, macros, triggers, automations, views and SLA policies. Note the oldest ticket date — history depth drives the whole timeline. Estimating from memory is the single most common cause of a blown migration window.
Data Profiler Get real record counts instead of estimating from memory -
Decide what history actually moves
Agree a cut-off with the support lead: all history, last 24 months, or open tickets plus a read-only archive. Every extra year of closed tickets adds API time and cost without adding much agent value. Get this in writing — it is the decision people relitigate mid-cutover.
A "move everything" default is what turns a two-week migration into a two-month one.
COI & ROI Calculator Build the 36-month business case you will need for sign-off -
Confirm Zendesk can hold your support model
Walk your current workflow through Zendesk: multi-brand, business hours, SLA targets, CSAT, side conversations, public vs internal notes, and any channel you depend on (voice, chat, WhatsApp, social). List anything with no native equivalent — those are project risks, not configuration details.
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Build the business case
Model licence delta, migration effort, agent retraining, and the cost of staying put (Cost of Inaction). Executives approve a number, not a plan, and you will be asked for it again at the go/no-go.
Helpdesk Migration Planner Turn ticket volume into a dated Kayako → Zendesk timeline -
Name owners and set the go/no-go date
One named owner each for data, configuration, integrations, and agent enablement, plus a decision-maker who can call a rollback. Put the go/no-go meeting in calendars now, 48 hours before the freeze.
Kayako → Zendesk specifics
- Integration ecosystem
- Zendesk's marketplace lists 1,500+ integrations (verify against Zendesk Marketplace for current count). Kayako lacks an app marketplace and relies on Zapier or Tray.io for third-party connections.
- Omnichannel gaps
- Kayako's native channels are limited to email, social media, and messaging — no native voice or SMS. Zendesk provides unified omnichannel ticketing across email, chat, voice, SMS, and social.
- Reporting limitations
- Kayako offers only four out-of-the-box dashboards, and custom reports must be exported to CSV. Zendesk Explore provides customizable, real-time analytics with pre-built and custom dashboards.
- AI investment
- Zendesk has invested in AI Agents, Intelligent Triage, and Copilot (launched 2023–2024). Kayako's AI capabilities are limited by comparison.
- Kayako Classic end-of-life risk
- Kayako Classic runs on end-of-life PHP 7.x (PHP 7.4 EOL was November 2022) and is in maintenance mode with no new features planned.
Don't move on until
- Record counts confirmed for tickets, contacts, organisations and macros
- Success criteria signed off by the support lead
- Freeze window provisionally booked with the business
02 Data Audit Find out what is actually in the data before you try to move it.
Objective A profiled, cleaned export with every quality defect either fixed at source or explicitly accepted.
Keep these open
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Take a full Kayako export and profile it
Export to CSV or JSON and profile every file: row counts, null rates per column, distinct values, and type consistency. Compare row counts against the API totals from Discovery — a gap here means your export is silently truncated, usually by pagination.
Data Profiler Profile the Kayako export for nulls, outliers and type drift -
Validate file structure before anyone writes a transform
Check delimiters, quoting, encoding (expect UTF-8, watch for BOMs and Latin-1), duplicate headers, and embedded newlines in ticket bodies. Ticket descriptions with raw newlines and commas break naive CSV parsers and silently shift columns.
A single unescaped quote in one ticket body can shift every subsequent column without any error.
CSV Validator Catch broken headers and ragged rows in the raw export -
Inventory PII and set retention
Scan for emails, phone numbers, payment card fragments, national IDs and anything else regulated in ticket bodies and custom fields — support tickets are where customers paste things they should not. Decide what gets migrated, masked, or dropped, and record the legal basis.
Ticket bodies and attachments routinely contain card and ID data that never appears in a structured field.
PII & Compliance Scanner Find regulated fields before they land in a new system -
Quantify duplicates, orphans and dead references
Count duplicate contacts (same email, different casing), tickets whose requester no longer exists, organisations with no members, and attachments whose parent ticket is gone. Fix these in Kayako where you can — migrating them just moves the mess.
Data Cleaner Strip empty rows, stray whitespace and dead columns -
Clean and normalise the export
Trim whitespace, drop empty rows and columns, normalise casing on emails and tags, and standardise every timestamp to UTC ISO 8601. Timezone drift is invisible at load time and shows up weeks later as SLA reports nobody can reconcile.
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Produce a masked copy for sandbox work
Generate a realistic but fake version of the export for testing and for any vendor who needs sample data. Loading real customer PII into a sandbox is a breach in most jurisdictions, and sandboxes are rarely covered by your DPA.
PII Masker Generate a safe copy for sandbox and vendor testing
Kayako → Zendesk specifics
- Kayako Journeys
- (customer activity timelines) have no Zendesk equivalent. You can approximate them by adding context to ticket tags or custom fields.
- Kayako Messenger conversations
- (real-time chat history) do not map natively to Zendesk Chat transcripts. These must be imported as tickets with a tag like source_kayako_messenger.
- Kayako Views
- must be recreated manually as Zendesk Views with equivalent filter logic.
- Historical SLA metrics and ticket performance data
- are not imported by Zendesk. Imported tickets do not run triggers, and ticket metrics such as first reply time and first resolution time are not backfilled. Snapshot your legacy reporting before cutover. (support.zendesk.com)
- Random sample audit
- Pull 50 random tickets across different statuses (open, closed, pending) and verify: correct requester, correct assignee/group, all comments present in order, correct timestamps, attachments accessible, private notes stayed private, and inline images render correctly.
Don't move on until
- Export parses cleanly with no ragged rows or encoding errors
- PII inventory complete and retention decisions recorded
- Duplicate and orphan records quantified and triaged
03 Field Mapping Turn two schemas into one signed-off mapping spec.
Objective A reviewed field-level mapping covering every object, with an explicit decision for every field that has no target.
Keep these open
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Generate the first-pass Kayako → Zendesk field map
Start from an automated match on both schemas, then review every row by hand. Automated matching gets the obvious 70% right and is confidently wrong on the rest — especially anything named "type", "status" or "custom_field_1".
Schema Mapper Opens pre-loaded with the Kayako → Zendesk field pair -
Map status, priority and channel values, not just field names
Enumerate every value in each picklist on both sides and map them explicitly. Value-level mismatches are the defect class that survives all the way to production because the field itself mapped fine — a ticket that should be "Pending" arriving as "Open" reopens SLA clocks.
Statuses with no target equivalent (on-hold, pending-customer) need a policy decision, not a best guess.
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Decide how custom fields land
Create the target custom fields first, matching type exactly (a dropdown mapped to free text can never be mapped back). Where Zendesk has no equivalent, decide between a new custom field, a tag, or a note appended to the ticket body — and record which.
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Resolve identity and threading
Decide how source IDs are preserved — most platforms will not let you set the primary key, so keep the original ID in a custom field. Without it, reconciliation becomes fuzzy matching and every future support question about an old ticket is unanswerable.
Losing the original ticket ID makes reconciliation and rollback effectively impossible.
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Plan attachments, inline images and threading order
Confirm size limits, allowed MIME types, and whether inline images survive as attachments or need rehosting. Decide the comment ordering and author attribution rules: comments loaded out of order, or all attributed to the API user, destroy the conversation history agents rely on.
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Freeze and sign off the mapping spec
Version the spec, walk the support lead through it row by row, and get explicit sign-off. Any change after this point goes through change control — mid-flight mapping edits are how partial loads happen.
Kayako → Zendesk specifics
- Custom field validation
- For each custom field, verify that values transferred correctly — especially picklist/dropdown fields where Kayako option IDs may not match Zendesk option IDs. Query 10 tickets per custom field type to confirm.
Don't move on until
- Every source field is mapped, deliberately dropped, or parked in a custom field
- Status, priority and channel value maps agreed with the support lead
- Mapping spec version-controlled and signed off
04 Test Migration Prove the pipeline on a small, representative slice.
Objective A pilot load into a Zendesk sandbox that reconciles cleanly and has been reviewed by real agents.
Keep these open
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Stand up a Zendesk sandbox that matches production config
Create the custom fields, groups, brands, business hours and SLA policies first. A pilot into a default sandbox tests nothing, because the failures you care about are all configuration mismatches.
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Pick a deliberately nasty pilot sample
Take 500-1000 records chosen for difficulty, not convenience: the longest ticket threads, tickets with the most attachments, non-Latin character sets, merged and split tickets, deleted requesters, and every status value. A clean random sample proves only that easy records are easy.
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Run the load with masked data and instrument everything
Log every API request and response with its source record ID. When 40 records fail out of 10,000 you need to know exactly which ones and why, without re-running the whole batch.
PII Masker Never load real customer PII into a sandbox -
Measure real throughput against the rate limit
Record achieved records-per-hour under Zendesk's actual rate limits, including retries and backoff. Extrapolate to the full volume: if the maths says the full load exceeds your freeze window, you fix that now, not on cutover night.
Published rate limits are ceilings, not throughput. Assume real-world rates are meaningfully lower once retries and backoff are counted.
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Reconcile the pilot and triage every failure
Diff source against target on record counts and field-level values. Every discrepancy gets a root cause and a fix — "probably fine" at pilot scale becomes thousands of broken records at full scale.
Migration Validation Tool Diff the pilot batch against source before scaling up -
Put real agents in front of the pilot data
Have two or three agents work sample tickets end to end in the sandbox. They find the things reconciliation cannot see: unreadable threading, missing context, macros that no longer make sense. Fix the mapping, then re-run.
Kayako → Zendesk specifics
- Attachment spot-check
- Download 20 random attachments from migrated tickets and verify they open correctly and are not corrupted 0-byte files. Pay special attention to attachments near the 20MB Kayako limit.
- Agent UAT
- Have 2–3 agents work their normal workflow in Zendesk for a day using real migrated tickets. Collect feedback on missing data or broken references. Provide agents with a feedback form covering: ticket history completeness, search functionality, custom field accuracy, and attachment accessibility.
- Poll job statuses
- For bulk imports, confirm all background jobs completed successfully before starting validation. (developer.zendesk.com)
- Email threading test
- Reply to an old Kayako notification email and verify whether Zendesk creates a new ticket (expected) or correctly routes it. Document the behavior for agent training.
Don't move on until
- Pilot batch reconciles to 100% on record counts
- Agents have reviewed sample tickets and confirmed they are workable
- Measured throughput extrapolates to a viable full-load window
05 Cutover Execute the switch inside a controlled, reversible window.
Objective All in-scope data live in Zendesk, agents working in the new system, and a rollback path that stayed available throughout.
Keep these open
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Pre-load history before the freeze
Load closed tickets and contacts days or weeks ahead while Kayako stays live. Only open tickets and the final delta need to move inside the freeze — this is the single biggest lever on window length.
Helpdesk Migration Planner Size the freeze window from Zendesk's real API limits -
Publish the runbook with times, owners and abort criteria
A timed sequence: freeze start, final export, delta load, channel switch, smoke test, go/no-go, agent switch. Name who does each step and the explicit condition that triggers a rollback. Decide the abort criteria before the night, when nobody wants to be the one to call it.
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Freeze Kayako and take the final delta
Stop new ticket creation, let agents finish in-flight replies, then export everything changed since the pre-load. Announce the freeze to the whole business, not just support — someone always tries to raise a ticket during it.
Tickets created during an unenforced freeze land in the old system and are the most common source of permanently lost data.
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Load the delta and open tickets
Run the delta load, then reconcile counts before touching any channel. Do not repoint email until the delta has verified — an inbound ticket arriving mid-load is far harder to untangle than a few extra minutes of freeze.
Migration Validation Tool Confirm the final delta landed before you reopen -
Repoint channels and verify with live traffic
Switch email forwarding and MX or connector settings, update chat widgets and web forms, and re-authorise integrations. Then send real test tickets through every channel and confirm each lands, routes and triggers the right automation.
Email forwarding changes can take up to a full DNS TTL to propagate — check the TTL days in advance and lower it if needed.
Cron Expression Builder Schedule the delta syncs that run through the freeze -
Run the go/no-go and switch the agents
Walk the exit criteria with the decision-maker, call it explicitly, then move agents over with a named person on hand for the first few hours. Keep Kayako read-only rather than cancelled — cancelling the old contract on day one removes your only fallback.
Don't move on until
- Full historical load complete and counts matched
- Inbound channels repointed and verified with live test tickets
- Rollback decision point passed explicitly, not by default
06 Validation Prove the migration is complete, then close it out.
Objective Documented evidence that data, workflow and reporting all survived, and a signed acceptance.
Keep these open
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Run the full reconciliation
Compare source and target on every object: total counts, counts by status, counts by group, attachment counts, and field-level spot checks on a random sample. Produce one report you can hand to an auditor.
Migration Validation Tool Reconcile Kayako and Zendesk record-for-record -
Verify field completeness, not just record counts
Re-profile the loaded data and compare null rates per field against the source profile. Matching record counts with a field that silently arrived empty is the failure mode counts alone will never catch.
Data Profiler Prove field completeness held up through the load -
Rebuild reporting and compare against baselines
Recreate your core dashboards — volume, first response time, resolution time, CSAT — and compare to pre-migration figures for the same period. Explain every variance; a changed SLA calculation is a real finding, not a rounding error.
SLA and first-response metrics are usually recalculated from the loaded timestamps, so they will differ if any timestamp mapping was approximate.
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Test the workflow layer end to end
Fire every trigger, automation, SLA escalation, macro and notification with a live ticket. Workflow does not migrate — it gets rebuilt — so it is untested until someone has actually watched it run.
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Confirm compliance and produce the audit trail
Re-scan the loaded data for regulated fields, confirm retention and deletion policies are configured in Zendesk, and file the evidence with your PII decisions from the audit phase.
PII & Compliance Scanner Produce the compliance evidence your auditor will ask for -
Sign off, then decommission on a schedule
Get written acceptance against the Discovery success criteria. Keep Kayako read-only for an agreed period (30-90 days is typical), take a final archive export, and only then cancel. Diarise the decommission date so it does not quietly renew.
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Record-count reconciliation
Compare total Organizations, Users, Tickets, and Comments between Kayako and Zendesk. Run a SQL COUNT() on your Kayako database (or use API total_count with &archived=1) and compare to Zendesk Search API results or the GET /api/v2/tickets/count endpoint. Allow for a small delta if the delta sync hasn't run yet.
Kayako → Zendesk specifics
- Search verification
- Search for 10 known tickets by subject line and requester email in Zendesk to confirm indexing. Wait for search indexing to complete (typically 2–5 minutes after bulk import) before running this test.
Don't move on until
- Full reconciliation report attached to the project record
- Reporting baselines match pre-migration figures within agreed tolerance
- Formal acceptance signed and archive retention scheduled
Field mapping reference
The field-by-field mapping for each object. Use this as the starting point for your mapping spec.
Kayako Zendesk Object Mapping
| Kayako field | Zendesk field | Notes |
|---|---|---|
| Cases (or Conversations) | Tickets | 1:1. Use Ticket Import API to preserve created_at timestamps. Store Kayako case ID in external_id and a visible custom field for agent lookup. |
| Messages (case replies) | Ticket Comments | Each message becomes a comment. Set public: true or false to match original visibility. Kayako "Messages" and "Posts" refer to the same underlying data — Messages are the API resource, Posts are the endpoint path. |
| Notes (internal) | Private Comments | Kayako Notes map to Zendesk comments with public: false. Notes may live outside the plain posts feed — audit note endpoints separately. |
| Users (customers) | Users (end-users) | Create before tickets. Match on email address. Zendesk requires unique emails; Kayako allows duplicates. |
| Agents / Staff | Users (agents) | Must exist in Zendesk before ticket import. License implications — each agent consumes a paid seat. |
| Organizations | Organizations | 1:1 mapping. Create before users. Configure domain mapping for automatic future user association. |
| Teams / Departments | Groups | Rebuild assignment rules manually after migration. |
| Tags | Tags | Direct mapping, but audit for naming conflicts and character restrictions (Zendesk tags are lowercase, no spaces). |
| Custom Fields | Custom Fields | Create in Zendesk first. Map field IDs. Picklist values must match exactly or the API rejects the ticket payload. |
| Attachments | Attachments | Upload via Zendesk Uploads API (/api/v2/uploads), then reference tokens in comment payloads. |
| SLAs | SLA Policies | Cannot be migrated. Must be rebuilt manually in Zendesk. |
| Triggers / Automations | Triggers / Automations | Cannot be migrated. Must be rebuilt manually. |
| Macros | Macros | Cannot be migrated. Must be rebuilt. |
| Help Center Articles | Help Center Articles | Separate migration via Help Center API. Kayako Classic's two-level hierarchy (Category → Article) must be adapted to Zendesk Guide's three-level hierarchy (Category → Section → Article). See the Help Center migration section below for details on images, metadata, and SEO redirects. |
| Satisfaction Ratings | Satisfaction Ratings | Can be set via Ticket Import API if score and comment data is available. |
| Collaborators | No clean equivalent | Requires a product decision, not just a field map. Options: add as CC'd users, store in a custom field, or convert to followers. |
Create Groups and Cus m Fields
| Kayako field | Zendesk field | Notes |
|---|---|---|
| Text | Text | Direct mapping |
| Select (single) | Drop-down | Tag values must match exactly |
| Multi-select | Multi-select | Available on Professional+ plans only |
| Checkbox | Checkbox | Maps to boolean |
| Radio buttons | Drop-down | Kayako radio → Zendesk drop-down; test tag generation |
| Linked select (cascading) | No native equivalent | Flatten to multiple independent drop-downs, or use conditional fields with a third-party app |
| File | No field-level equivalent | Store as attachments on the ticket |
What breaks
Known failure modes. Have a recovery plan for each before you cut over.
Archived cases silently omitted
The default API call excludes tickets closed more than 30 days ago unless &archived=1 is appended. (help.kayako.com)
Duplicate users
Kayako allows multiple user records with the same email. Zendesk does not. Your script must deduplicate before import — the Zendesk API returns 422 for duplicate emails.
Invalid emails
Zendesk strictly enforces email RFC standards. Users with malformed emails (missing TLDs, invalid characters) will be rejected. Sanitize email strings or assign placeholder addresses.
Inline images in messages
Kayako stores inline images as embedded URLs pointing to the Kayako instance (or as base64-encoded content). After migration, these URLs break unless you re-host the images on Zendesk and update the HTML body's src tags. See Step 8 above for implementation.
Kayako Classic two-level KB hierarchy
Kayako Classic allows articles directly under Categories without Folders. Zendesk Guide requires three levels (Category → Section → Article). Create placeholder Sections for orphaned articles.
Multi-brand instances
Kayako's brand-level data separation may not map cleanly to Zendesk's multi-brand architecture. In Zendesk, each brand has its own subdomain, Help Center, and email addresses, but shares a single ticket pool. Each brand needs its own extraction and mapping pass. Ensure tickets are tagged or routed to the correct Zendesk brand during import using the brand_id field on the ticket payload.
Custom field type mismatches
Kayako supports field types that don't exist in Zendesk (and vice versa). Audit field types before migration. Zendesk does not allow changing a field's type after creation. (support.zendesk.com)
total_count drift
Kayako's total_count response field can change between paginated API calls if records are created or modified during extraction. Treat extraction as a point-in-time snapshot and reconcile with a delta sync.
Kayako posts omit activities by default
Use filters=ALL to get complete timeline data. (developer.kayako.com)
Zendesk comment and thread limits are hard limits
65,535 characters per comment and 5,000 comments per ticket. Route oversized threads to a manual review queue. (support.zendesk.com)
Zendesk search indexing lags
After bulk import, search may take several minutes to index new records. Wait for indexing before UI-based validation.
Timezone mismatches
Kayako may store timestamps in the server's local timezone (especially Classic). Zendesk expects UTC. Verify timezone handling in your ETL pipeline to avoid shifted timestamps.
Tools used in this playbook
All free, all run entirely in your browser — nothing is uploaded.
FAQ
How long does a Kayako to Zendesk migration take?
A typical migration takes 1–3 weeks with an in-house engineering team, or 3–5 business days with a managed service. The primary variables are ticket volume, attachment count, and number of custom fields requiring transformation.
Can I migrate Kayako to Zendesk without losing data?
Yes, but only if your extraction includes the &archived=1 parameter when calling the Kayako Cases API. Without it, all tickets closed more than 30 days ago are silently excluded. Attachments over 20MB per post may also fail with a 402 error and require manual handling.
What data cannot be migrated from Kayako to Zendesk?
Kayako Macros, Triggers, SLA Policies, Automations, and Views cannot be migrated programmatically and must be manually rebuilt in Zendesk. Kayako Journeys have no Zendesk equivalent. Ticket ID numbers are not preserved — Zendesk assigns new IDs. Imported tickets do not carry ticket metrics like first reply time or resolution time.
Is there a native Kayako-to-Zendesk migration tool?
No. Neither Kayako nor Zendesk provides a native migration tool between the two platforms. Zendesk's built-in CSV import handles users and organizations but not full ticket history with comments and attachments. The Ticket Import API (POST /api/v2/imports/tickets) is the correct endpoint for migration.
Should I use the Kayako API or request a MySQL dump?
Use the API when you need controlled extraction, interval syncs, or a final delta before cutover. Use a MySQL dump when completeness and volume matter more than convenience — especially for archived or attachment-heavy instances. Kayako delivers dumps in MySQL format only (no CSV), and download links expire within 1–7 days.