Pipedrive to HubSpot migration usually gets judged on one check: do the deals show up. That check passes reliably, contacts, companies and deals map cleanly, and the migration gets marked complete. Three other things quietly do not transfer the way the rest of the migration implies, and each has a different, specific, checkable reason, not a vague “some data loss is normal” caveat.
Pipedrive to HubSpot Migration Looks Complete Before It Actually Is
The core CRM objects genuinely do transfer well, which is exactly why the migration reads as finished sooner than it actually is. Per HubSpot’s own documentation on Smart Transfer, Pipedrive’s objects map directly onto HubSpot’s own: People becomes Contacts, Pipedrive’s Organisations object becomes Companies, and Deals stays Deals, alongside activity types, Email, Meeting, Call and Task Activities, Notes, Products, Currencies and Users. A team that opens HubSpot after a migration, sees its contacts and deals sitting where they should, and calls the job done is checking the part of the migration that was always going to work.
Field-level reconciliation is handled more carefully than a simple copy-paste, which is worth knowing because it shows the transfer is doing real mapping work, not a blind field dump. HubSpot’s own documentation on Smart Transfer gives a worked example: “Pipedrive has multiple fields for the close date of a deal. HubSpot Smart Transfer will create a workflow that fills the Close date property in HubSpot with the value from the correct field in Pipedrive.” That is a genuinely useful piece of migration engineering, and it is also a clue that other, less carefully-handled data categories exist elsewhere in the same transfer.
What Transfers Cleanly and What Doesn’t
Custom objects are the first category, and the gap here is total rather than partial: “the transfer of custom objects isn’t supported by HubSpot Smart Transfer.” Any custom object built in Pipedrive, not a standard Person, Organisation or Deal, has no transfer path through Smart Transfer at all. A team that built meaningful structure on top of Pipedrive’s standard objects needs a separate migration plan for that data before assuming Smart Transfer covers everything.
Attachments are the second category, and the gap is subtler: they do transfer, but only once. Per HubSpot’s own documentation, attachments are among the data types that “can be transferred to HubSpot with a one-time post-sync transfer,” and critically, “the data transferred through one-time post-sync transfers will not be part of an ongoing sync and therefore will not automatically stay up to date.” A file attached to a Pipedrive deal after that one-time transfer runs simply will not appear in HubSpot on its own, and neither HubSpot’s Smart Transfer documentation nor its migration guide describes a way to manually re-trigger a one-time post-sync transfer for records added afterwards, which is worth confirming directly with HubSpot rather than assuming a repeat transfer is available on demand.
Activity syncing is the third category, and it is the one most likely to catch a team by surprise because it depends on which HubSpot subscription is active, not on anything about the data itself. HubSpot’s own documentation states plainly that “a Data Hub subscription is required to sync Pipedrive activities to HubSpot,” while the broader Smart Transfer feature is available with “all products and plans.” A team migrating on Sales Hub Professional without Data Hub gets contacts, companies and deals transferred correctly, but calls, emails, meetings and tasks simply do not sync, not because anything failed, but because the specific subscription that activity sync depends on was never part of the plan.
Checking the Migration Actually Worked
None of these three gaps is a defect in Smart Transfer. Each is a documented, deliberate boundary of what the tool is built to do, which is exactly why they are easy to miss: the transfer results report success against what Smart Transfer actually set out to do, and neither HubSpot source document describes an error or warning specific to any of the three gaps, which is worth confirming directly with HubSpot rather than assuming one would appear. The practical implication is that “did the migration succeed” and “does the HubSpot portal now hold everything the team expects it to hold” are two different questions, and only the first one gets answered automatically. Answering the second one is a deliberate, five-minute check against the three categories above, done once, before the migration is signed off as finished and the Pipedrive account gets decommissioned.
HubSpot’s own migration process guide puts an audit step first for a reason: “audit your data: run an audit of the data that you want to transfer to HubSpot,” before any configuration or sync begins. Confirming contacts, companies and deals landed is the easy, obvious check, and it is worth doing, but it only verifies the part of the migration that was always going to work. The harder, more useful check is specific to each gap: for custom objects, confirm before migration starts whether any exist in the Pipedrive account at all, since there is no post-migration fix through Smart Transfer if one turns up afterwards. For attachments, account for the fact that only a one-time snapshot ran and confirm with HubSpot directly what, if anything, catches up files attached after that point, rather than assuming files are still syncing. For activities, confirm whether Data Hub is actually part of the plan before assuming call and meeting history is coming across; a missing Data Hub subscription shows up as simply empty activity timelines, and whether the transfer results themselves call out that gap is worth confirming directly with HubSpot rather than assuming.
Spot-checking a handful of records that are known to have all three, a deal with an attachment, a deal with logged calls, and confirming whether any custom-object data existed in Pipedrive in the first place, catches all three gaps in one pass rather than discovering each one separately, weeks apart, when someone eventually goes looking for something that quietly did not come across. Building that spot check into the migration’s own sign-off step, rather than treating “the contacts are there” as the finish line, is the difference between a migration that looks complete and one that actually is.
Where Teams Get This Wrong
The pattern behind all five mistakes below is the same one: each gap looks identical to “there was nothing there to begin with” from inside HubSpot after the fact. A missing custom object, a stale attachment, an empty activity timeline and an assumed-but-unconfirmed backfill are all easy to mistake for a genuinely empty record, so nobody notices until a specific piece of data is needed and turns out to be missing, sometimes months after the migration itself is long forgotten.
The most common mistake is treating “contacts and deals look right” as proof the whole migration succeeded, when that check only ever covered the part of Smart Transfer that reliably works.
The second common mistake is assuming attachments are part of the ongoing sync because everything else is. They are not: a one-time post-sync transfer runs once, and anything attached to a Pipedrive record afterwards is invisible to HubSpot with no documented way to manually catch it up, which is worth confirming directly with HubSpot rather than assuming.
The third common mistake is not checking the HubSpot subscription tier before migrating and assuming activity history comes across by default. Data Hub specifically gates activity syncing, so a team on a plan without it gets a CRM that looks migrated but has empty call and meeting timelines, and whether the transfer results themselves call out that gap is worth confirming directly with HubSpot rather than assuming.
The fourth common mistake is discovering custom objects exist in the source Pipedrive account only after the migration has already run, at which point there is no supported transfer path for them through Smart Transfer at all. Auditing for custom objects before migration starts is the only point at which this gap can actually be planned around rather than worked around afterwards.
The fifth common mistake is assuming a later subscription upgrade to add Data Hub will automatically backfill activity history that never synced during the original migration. Whether an upgrade retroactively pulls across historical calls, emails and meetings or only starts syncing new activity going forward is worth confirming directly with HubSpot before relying on an upgrade to quietly fix a gap discovered after the fact, rather than assuming either way.
Related Reading
For the automation side of keeping Pipedrive and other tools enriched before or during a migration, see Automate Pipedrive Contact Enrichment with Clearbit and n8n. For the CRM foundation this migration is moving data into, see HubSpot Consultancy. For the data-quality side of a freshly migrated portal, see HubSpot CRM Data Management: Clean Data, Automation and Lead Scoring.
Go deeper: HubSpot Lifecycle Management: Contacts vs Custom Objects · Salesforce to HubSpot Sync · RevOps Consultancy
Frequently Asked Questions
Do custom objects transfer when migrating from Pipedrive to HubSpot?
No. HubSpot’s own documentation states plainly that the transfer of custom objects isn’t supported by Smart Transfer at all. Any custom object built in Pipedrive needs a separate migration plan, since there is no supported path for it through the standard migration tool.
Do file attachments keep syncing after a Pipedrive to HubSpot migration?
No. Attachments transfer through a one-time post-sync transfer, not the ongoing sync that covers contacts, companies and deals. Anything attached to a Pipedrive record after that one-time transfer runs will not automatically appear in HubSpot, and neither HubSpot’s Smart Transfer nor migration documentation describes a way to manually re-trigger that transfer for records added afterwards.
Why might call and meeting history be missing after a Pipedrive migration?
Because activity syncing specifically requires a Data Hub subscription. Core objects like contacts, companies and deals transfer on any HubSpot plan, but calls, emails, meetings and tasks only sync if Data Hub is part of the account’s subscription, and the gap shows up as simply empty activity timelines; whether the transfer results themselves flag this is worth confirming directly with HubSpot rather than assuming.
What’s the single most important check before starting a Pipedrive to HubSpot migration?
Auditing the Pipedrive account for custom objects before migration begins. Custom objects have no supported transfer path through Smart Transfer once the migration is already underway, and unlike a missed activity sync, there is no subscription change worth checking afterwards, since custom objects have no equivalent path to fall back on at all.