diff --git a/.changeset/rare-pigs-divide.md b/.changeset/rare-pigs-divide.md
new file mode 100644
index 0000000000..de8450782f
--- /dev/null
+++ b/.changeset/rare-pigs-divide.md
@@ -0,0 +1,5 @@
+---
+"claude-dev": patch
+---
+
+Fix checking "Support Images" setting had no effect on first click
diff --git a/webview-ui/src/components/settings/ApiOptions.tsx b/webview-ui/src/components/settings/ApiOptions.tsx
index 3d6037e275..4929d43876 100644
--- a/webview-ui/src/components/settings/ApiOptions.tsx
+++ b/webview-ui/src/components/settings/ApiOptions.tsx
@@ -721,7 +721,7 @@ const ApiOptions = ({ showModelOptions, apiErrorMessage, modelIdErrorMessage, is
 					{modelConfigurationSelected && (
 						<>
 							<VSCodeCheckbox
-								checked={apiConfiguration?.openAiModelInfo?.supportsImages}
+								checked={!!apiConfiguration?.openAiModelInfo?.supportsImages}
 								onChange={(e: any) => {
 									const isChecked = e.target.checked === true
 									let modelInfo = apiConfiguration?.openAiModelInfo