diff --git a/changelog/fragments/1669234779-Fix-upgrade-under-V2.yaml b/changelog/fragments/1669234779-Fix-upgrade-under-V2.yaml
new file mode 100644
index 00000000000..d659b62d815
--- /dev/null
+++ b/changelog/fragments/1669234779-Fix-upgrade-under-V2.yaml
@@ -0,0 +1,31 @@
+# Kind can be one of:
+# - breaking-change: a change to previously-documented behavior
+# - deprecation: functionality that is being removed in a later release
+# - bug-fix: fixes a problem in a previous version
+# - enhancement: extends functionality but does not break or fix existing behavior
+# - feature: new functionality
+# - known-issue: problems that we are aware of in a given version
+# - security: impacts on the security of a product or a user’s deployment.
+# - upgrade: important information for someone upgrading from a prior version
+# - other: does not fit into any of the other categories
+kind: bug-fix
+
+# Change summary; a 80ish characters long description of the change.
+summary: Fix upgrade under V2
+
+# Long description; in case the summary is not enough to describe the change
+# this field accommodate a description without length limits.
+#description:
+
+# Affected component; a word indicating the component this changeset affects.
+component: Fix a typo that was preventing upgrades under V2.
+
+# PR number; optional; the PR number that added the changeset.
+# If not present is automatically filled by the tooling finding the PR where this changelog fragment has been added.
+# NOTE: the tooling supports backports, so it's able to fill the original PR number instead of the backport PR number.
+# Please provide it if you are adding a fragment for a different PR.
+pr: 1779
+
+# Issue number; optional; the GitHub issue related to this changeset (either closes or is part of).
+# If not present is automatically filled by the tooling with the issue linked to the PR number.
+#issue: 1234
diff --git a/internal/pkg/agent/application/coordinator/coordinator.go b/internal/pkg/agent/application/coordinator/coordinator.go
index 48a476a5164..e6dbe44c037 100644
--- a/internal/pkg/agent/application/coordinator/coordinator.go
+++ b/internal/pkg/agent/application/coordinator/coordinator.go
@@ -255,7 +255,7 @@ func (c *Coordinator) ReExec(callback reexec.ShutdownCallbackFn, argOverrides ..
 // Upgrade runs the upgrade process.
 func (c *Coordinator) Upgrade(ctx context.Context, version string, sourceURI string, action *fleetapi.ActionUpgrade) error {
 	// early check outside of upgrader before overridding the state
-	if c.upgradeMgr.Upgradeable() {
+	if !c.upgradeMgr.Upgradeable() {
 		return ErrNotUpgradable
 	}