Migrating from Zendesk to Trengo requires translating data across significantly different platform architectures. Zendesk's ticket-centric model with Organizations, Groups, and custom statuses must be mapped to Trengo's Contact Groups, Departments, and Labels system. Trengo enforces strict API rate limits of approximately 60 requests per minute for conversation history imports. Attachments must be downloaded from Zendesk, uploaded to Trengo separately, and then referenced by file ID in message payloads. Every migration requires pre-building Custom Fields, Teams, and Help Center scaffolding before data transfer, along with careful HTML sanitization and strict throttling of bulk API requests to navigate platform limits.
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 Zendesk
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 Trengo can hold your support model
Walk your current workflow through Trengo: 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 Zendesk → Trengo 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.
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Establish Teams and Labels
Create your organizational structure: import your existing Zendesk Groups as Teams in Trengo. Simultaneously, replicate your global system of Tags as Labels in Trengo. These form the backbone for ticket routing and organizational tagging.
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Build Help Center Scaffolding
Set up the structure of your Knowledge Base (KB). This involves creating top-level Help Centers, followed by Categories, and then the Sections within them.
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 Zendesk 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 Zendesk 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 Zendesk 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
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 Zendesk → Trengo 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 Zendesk → Trengo 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 Trengo 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.
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Define Custom Fields
Start by mirroring the schema of your Zendesk User Fields and Organization Fields by creating corresponding Custom Fields within Trengo. This step is critical because users and tickets cannot accept custom data until these fields are defined first.
Zendesk → Trengo specifics
- Maintain your ID mapping table
- (Zendesk IDs → Trengo IDs) as the authoritative reference. If a partial migration fails, this table tells you exactly which records made it across and which did not.
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 Trengo sandbox that reconciles cleanly and has been reviewed by real agents.
Keep these open
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Stand up a Trengo 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 Trengo'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.
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 Trengo, 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 Zendesk 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 Trengo'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 Zendesk 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 Zendesk read-only rather than cancelled — cancelling the old contract on day one removes your only fallback.
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Keep Zendesk active
until validation is complete. Do not cancel your Zendesk subscription or delete data until the migration is fully verified.
Zendesk → Trengo specifics
- If migration fails mid-way
- Because Trengo is the write target, you can delete the partially imported data in Trengo and re-run from the last known good checkpoint using your mapping table. The source Zendesk data is never modified during the migration.
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 Zendesk and Trengo 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 Trengo, 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 Zendesk 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.
Zendesk → Trengo specifics
- Users/Contacts
- Compare the total count of migrated users and contacts against the source Zendesk instance. Query both platforms and reconcile the numbers.
- Conversations
- For a sample set of tickets, verify that the message count per ticket matches the original and that messages appear in the correct chronological order with correct authorship.
- Knowledge Base
- Confirm article counts per section match. Open a sample of articles and verify that embedded images render correctly from their new Trengo-hosted URLs.
- Attachments
- Verify that attachments on sampled tickets are downloadable and match the original file size.
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.
Zendesk Trengo Object Mapping
| Zendesk field | Trengo field | Notes |
|---|---|---|
| Users (Agents) | Users | Role mapping required (admin, agent, etc.) |
| End Users | Contacts / Profiles | |
| Organizations | Contact Groups | Membership association requires post-creation updates |
| Groups | Teams | |
| Tags | Labels | |
| Custom User Fields | Custom Contact Fields | Field types may not map 1:1; validate dropdown options |
| Custom Organization Fields | Custom Contact Group Fields | |
| Custom Ticket Fields | Custom Ticket Fields | Conditional logic is lost; must be rebuilt manually |
| Ticket Forms | No direct equivalent | Must be manually recreated; conditional rules do not transfer |
| Ticket Statuses (custom) | Custom Statuses | Granular custom statuses require manual definition |
| Tickets | Tickets | Status, priority, assignment metadata transfers; internal notes map to internal messages |
| Ticket Comments (public) | Ticket Messages (external) | HTML content may need sanitization |
| Ticket Comments (internal) | Ticket Messages (internal) | |
| Attachments | Attachments | Must be re-uploaded; new Trengo file IDs replace original URLs |
| Help Centers | Help Centers | |
| Categories | Categories | |
| Sections | Sections | |
| Articles | Articles | Embedded media URLs must be rewritten to Trengo-hosted references |
| Article Comments | No API support | Currently no standardized Trengo API for importing historical article comments |
| Triggers | Rules | Must be manually rebuilt; logic structures differ |
| Automations | Rules | Must be manually rebuilt |
| Macros | Quick Replies / Rules | Partial parity; complex macros have no direct equivalent |
| SLA Policies | No direct equivalent | SLA breach history cannot be imported retroactively |
| Views | No direct equivalent | Must be recreated using Trengo's filtering/view system |
| Ticket Metric Events | Not importable | Historical metrics (SLA breach events, response times) are not importable |
| Satisfaction Ratings (CSAT) | Not importable | Historical CSAT scores do not transfer |
Risk matrix
Per-object risk for this pair. Plan extra validation around anything marked high.
| Object | Risk | Notes |
|---|---|---|
| Tickets | low | Core ticket metadata (priority, status, assignments) maps to Trengo tickets. |
| Conversation History | medium | Must be injected sequentially preserving authorship and timestamps using specialized import mechanisms. |
| Organizations | medium | Map to Trengo Contact Groups. Bulk import of group memberships requires programmatic updates. |
| Attachments | medium | Require separate upload to Trengo and re-linking by file ID in message payloads. |
| Help Center Content | low | Categories, sections, and articles can be moved via API with media re-hosting. |
| Custom Ticket Statuses | medium | Granular custom statuses must be manually recreated and mapped in Trengo. |
| Article Comments | high | No standardized Trengo API for creating historical article comments. |
| SLA Metrics / Audit Logs | high | Cannot be imported retroactively. Must be archived from the source system. |
| Triggers / Automations | high | Must be completely rebuilt in Trengo's rule engine. |
The hard parts
What makes this specific migration difficult, beyond the mechanics.
Strict Rate Limits
Trengo APIs enforce approximately 60 requests per minute for conversation imports. Mass import requires careful throttling to avoid 429 errors.
Attachment Re-linking
Files must be uploaded separately to Trengo and the resulting file ID referenced in message import payloads to keep files linked to the correct historical comment.
HTML Sanitization
Complex HTML from Zendesk ticket comments can cause display issues in Trengo. Elements must be sanitized and adapted to the correct import channel format.
Metadata Loss
Granular SLA breach events, skip records, and metric events cannot be inserted retroactively into Trengo. The original Zendesk instance must be kept for archival reporting.
Tools used in this playbook
All free, all run entirely in your browser — nothing is uploaded.