diff --git a/server/fleet/apple_mdm.go b/server/fleet/apple_mdm.go
index 52cc924565..3752f89d38 100644
--- a/server/fleet/apple_mdm.go
+++ b/server/fleet/apple_mdm.go
@@ -1129,14 +1129,14 @@ func (r *MDMAppleRawActivation) ValidateUserProvided(configurationIdentifier str
 	invalid := &InvalidArgumentError{}
 
 	if strings.TrimSpace(r.Type) == "" {
-		invalid.Append("Type", "Activation must include a Type.")
+		invalid.Append("Type", "The custom activation must include a Type.")
 	} else if !strings.HasPrefix(r.Type, MDMAppleActivationTypePrefix) {
 		invalid.Append("Type", fmt.Sprintf("Only activation declarations (%s) are supported.", MDMAppleActivationTypePrefix))
 	}
 
 	switch {
 	case strings.TrimSpace(r.Identifier) == "":
-		invalid.Append("Identifier", "Activation must include an Identifier.")
+		invalid.Append("Identifier", "The custom activation must include an Identifier.")
 	case len(r.Identifier) > MDMAppleDeclarationIdentifierMaxLen:
 		invalid.Append("Identifier", fmt.Sprintf(
 			"Identifier must be %d bytes or fewer.", MDMAppleDeclarationIdentifierMaxLen))
@@ -1144,12 +1144,12 @@ func (r *MDMAppleRawActivation) ValidateUserProvided(configurationIdentifier str
 
 	switch configs := r.Payload.StandardConfigurations; {
 	case len(configs) == 0:
-		invalid.Append("StandardConfigurations", "Activation must reference the configuration profile it's uploaded with.")
+		invalid.Append("StandardConfigurations", "The custom activation must reference the identifier of the configuration profile used to upload it.")
 	case len(configs) > 1:
-		invalid.Append("StandardConfigurations", "Activation can only reference one configuration profile.")
+		invalid.Append("StandardConfigurations", "The custom activation can only have one referenced configuration profile. Learn more: https://fleetdm.com/learn-more-about/ddm-activations")
 	case configs[0] != configurationIdentifier:
 		invalid.Append("StandardConfigurations", fmt.Sprintf(
-			"Activation must reference the configuration profile it's uploaded with. Expected %q, got %q.",
+			"The custom activation must reference the identifier of the configuration profile used to upload it. Expected %q, got %q.",
 			configurationIdentifier, configs[0]))
 	}
 
diff --git a/server/fleet/apple_mdm_test.go b/server/fleet/apple_mdm_test.go
index a893011664..ede13abe22 100644
--- a/server/fleet/apple_mdm_test.go
+++ b/server/fleet/apple_mdm_test.go
@@ -1235,13 +1235,13 @@ func TestMDMAppleRawActivationValidateUserProvided(t *testing.T) {
 			name:        "missing type",
 			activation:  rawActivation("", "com.fleet.act.passcode", configIdentifier),
 			wantErr:     true,
-			errContains: "Activation must include a Type.",
+			errContains: "The custom activation must include a Type.",
 		},
 		{
 			name:        "whitespace type",
 			activation:  rawActivation("      ", "com.fleet.act.passcode", configIdentifier),
 			wantErr:     true,
-			errContains: "Activation must include a Type.",
+			errContains: "The custom activation must include a Type.",
 		},
 		{
 			name: "configuration type is not an activation",
@@ -1254,7 +1254,7 @@ func TestMDMAppleRawActivationValidateUserProvided(t *testing.T) {
 			name:        "missing identifier",
 			activation:  rawActivation("com.apple.activation.simple", "   ", configIdentifier),
 			wantErr:     true,
-			errContains: "Activation must include an Identifier.",
+			errContains: "The custom activation must include an Identifier.",
 		},
 		{
 			name:        "identifier over Apple's 64 octet limit",
@@ -1266,14 +1266,14 @@ func TestMDMAppleRawActivationValidateUserProvided(t *testing.T) {
 			name:        "no configurations referenced",
 			activation:  rawActivation("com.apple.activation.simple", "com.fleet.act.passcode"),
 			wantErr:     true,
-			errContains: "Activation must reference the configuration profile it's uploaded with.",
+			errContains: "The custom activation must reference the identifier of the configuration profile used to upload it.",
 		},
 		{
 			name: "more than one configuration referenced",
 			activation: rawActivation("com.apple.activation.simple", "com.fleet.act.passcode",
 				configIdentifier, "com.fleet.cfg.firewall"),
 			wantErr:     true,
-			errContains: "Activation can only reference one configuration profile.",
+			errContains: "The custom activation can only have one referenced configuration profile.",
 		},
 		{
 			name: "references a different configuration",
diff --git a/server/service/apple_mdm_test.go b/server/service/apple_mdm_test.go
index 37e030f9f1..24b4dfc1c5 100644
--- a/server/service/apple_mdm_test.go
+++ b/server/service/apple_mdm_test.go
@@ -9993,7 +9993,7 @@ func TestNewMDMAppleDeclarationWithActivation(t *testing.T) {
 		activation := activationBytesForTest("com.fleet.actD1", "com.fleet.configOther")
 
 		_, err := svc.NewMDMAppleDeclaration(ctx, 0, decl, nil, "name", fleet.LabelsIncludeAll, nil, activation)
-		require.ErrorContains(t, err, "Activation must reference the configuration profile it's uploaded with")
+		require.ErrorContains(t, err, "The custom activation must reference the identifier of the configuration profile used to upload it")
 	})
 
 	t.Run("malformed activation is rejected", func(t *testing.T) {