diff --git a/tools/importer-rest-api-specs/internal/components/apidefinitions/parser/dataworkarounds/workaround_automation.go b/tools/importer-rest-api-specs/internal/components/apidefinitions/parser/dataworkarounds/workaround_automation.go
new file mode 100644
index 0000000000..7ca9d32d72
--- /dev/null
+++ b/tools/importer-rest-api-specs/internal/components/apidefinitions/parser/dataworkarounds/workaround_automation.go
@@ -0,0 +1,66 @@
+package dataworkarounds
+
+import (
+	"errors"
+	"fmt"
+
+	sdkModels "github.com/hashicorp/pandora/tools/data-api-sdk/v1/models"
+)
+
+// Workaround for a type change on typespec migration
+// request/response object types changed to `string` which is problematic for go-azure-sdk
+var _ workaround = WorkaroundAutomation42369{}
+
+type WorkaroundAutomation42369 struct{}
+
+func (w WorkaroundAutomation42369) IsApplicable(serviceName string, apiVersion sdkModels.APIVersion) bool {
+	return serviceName == "Automation" && apiVersion.APIVersion == "2024-10-23"
+}
+
+func (w WorkaroundAutomation42369) Name() string {
+	return "Automation / 42369"
+}
+
+func (w WorkaroundAutomation42369) Process(input sdkModels.APIVersion) (*sdkModels.APIVersion, error) {
+	runbook, ok := input.Resources["Runbook"]
+	if !ok {
+		return nil, errors.New("expected a `Runbook` resource but didn't get one")
+	}
+
+	runbookDraft, ok := input.Resources["RunbookDraft"]
+	if !ok {
+		return nil, errors.New("expected a `RunbookDraft` resource but didn't get one")
+	}
+
+	for _, resource := range []sdkModels.APIResource{runbook, runbookDraft} {
+		operation, ok := resource.Operations["GetContent"]
+		if !ok {
+			return nil, fmt.Errorf("%s - expected an Operation named `GetContent` but didn't get one", resource.Name)
+		}
+		if operation.ResponseObject == nil {
+			return nil, fmt.Errorf("%s - expected a non-nil ResponseObject for Operation named `GetContent`", resource.Name)
+		}
+		if operation.ResponseObject.Type == sdkModels.RawFileSDKObjectDefinitionType {
+			return nil, fmt.Errorf("%s - expected ResponseObject.Type for Operation named `GetContent` to not be %s, this workaround can be removed", resource.Name, sdkModels.RawFileSDKObjectDefinitionType)
+		}
+		operation.ResponseObject.Type = sdkModels.RawFileSDKObjectDefinitionType
+		resource.Operations["GetContent"] = operation
+	}
+
+	operation, ok := runbookDraft.Operations["ReplaceContent"]
+	if !ok {
+		return nil, errors.New("expected an Operation named `ReplaceContent` but didn't get one")
+	}
+	if operation.RequestObject == nil {
+		return nil, errors.New("expected a non-nil RequestObject for Operation named `ReplaceContent`")
+	}
+	if operation.RequestObject.Type == sdkModels.RawFileSDKObjectDefinitionType {
+		return nil, fmt.Errorf("expected RequestObject.Type for Operation named `ReplaceContent` to not be %s, this workaround can be removed", sdkModels.RawFileSDKObjectDefinitionType)
+	}
+	operation.RequestObject.Type = sdkModels.RawFileSDKObjectDefinitionType
+	runbookDraft.Operations["ReplaceContent"] = operation
+
+	input.Resources["Runbook"] = runbook
+	input.Resources["RunbookDraft"] = runbookDraft
+	return &input, nil
+}
diff --git a/tools/importer-rest-api-specs/internal/components/apidefinitions/parser/dataworkarounds/workarounds.go b/tools/importer-rest-api-specs/internal/components/apidefinitions/parser/dataworkarounds/workarounds.go
index dbf3d42b13..6792f4f6ae 100644
--- a/tools/importer-rest-api-specs/internal/components/apidefinitions/parser/dataworkarounds/workarounds.go
+++ b/tools/importer-rest-api-specs/internal/components/apidefinitions/parser/dataworkarounds/workarounds.go
@@ -19,6 +19,7 @@ var workarounds = []workaround{
 	workaroundAlertsManagement{},
 	workaroundApiManagement39054{},
 	workaroundAuthorization25080{},
+	WorkaroundAutomation42369{},
 	workaroundAutomation25108{},
 	workaroundAutomation25435{},
 	workaroundBatch21291{},