diff --git a/content/master/guides/upgrade-crossplane.md b/content/master/guides/upgrade-crossplane.md
index 33be43c1..c2339852 100644
--- a/content/master/guides/upgrade-crossplane.md
+++ b/content/master/guides/upgrade-crossplane.md
@@ -7,10 +7,20 @@ description: "Upgrade Crossplane to newer versions"
 The recommended upgrade method for an existing Crossplane install is to use
 [Helm](http://helm.io).
 
+<!-- vale write-good.Weasel = NO -->
+{{<hint "important" >}}
+Always upgrade Crossplane **one minor version at a time**, using the most recent
+patch version available for each.
+
+For example, if you are on `v1.18` and want to upgrade to `v2.0`, you should
+first upgrade to `v1.19`, then `v1.20`, before finally upgrading to `v2.0`. The
+upgrade path in this example looks like `v1.18` → `v1.19` → `v1.20` → `v2.0`.
+{{</hint>}}
+<!-- vale write-good.Weasel = YES -->
+
 ## Prerequisites
 * [Helm](https://helm.sh/docs/intro/install/) version `v3.2.0` or later
 
-
 ## Add the Crossplane Helm repository
 Verify Helm has the Crossplane repository.
 
@@ -29,7 +39,7 @@ helm repo update
 {{<hint "important" >}}
 Upgrading Crossplane without updating the Helm chart installs the last version
 available in the locally cached Helm chart.
-{{< /hint >}}
+{{</hint>}}
 
 ## Upgrade Crossplane
 
diff --git a/content/v2.0/guides/upgrade-crossplane.md b/content/v2.0/guides/upgrade-crossplane.md
index 33be43c1..c2339852 100644
--- a/content/v2.0/guides/upgrade-crossplane.md
+++ b/content/v2.0/guides/upgrade-crossplane.md
@@ -7,10 +7,20 @@ description: "Upgrade Crossplane to newer versions"
 The recommended upgrade method for an existing Crossplane install is to use
 [Helm](http://helm.io).
 
+<!-- vale write-good.Weasel = NO -->
+{{<hint "important" >}}
+Always upgrade Crossplane **one minor version at a time**, using the most recent
+patch version available for each.
+
+For example, if you are on `v1.18` and want to upgrade to `v2.0`, you should
+first upgrade to `v1.19`, then `v1.20`, before finally upgrading to `v2.0`. The
+upgrade path in this example looks like `v1.18` → `v1.19` → `v1.20` → `v2.0`.
+{{</hint>}}
+<!-- vale write-good.Weasel = YES -->
+
 ## Prerequisites
 * [Helm](https://helm.sh/docs/intro/install/) version `v3.2.0` or later
 
-
 ## Add the Crossplane Helm repository
 Verify Helm has the Crossplane repository.
 
@@ -29,7 +39,7 @@ helm repo update
 {{<hint "important" >}}
 Upgrading Crossplane without updating the Helm chart installs the last version
 available in the locally cached Helm chart.
-{{< /hint >}}
+{{</hint>}}
 
 ## Upgrade Crossplane