diff --git a/.changes/next-release/bugfix-7029c1d5-212c-48ac-9513-38f0beca8fa8.json b/.changes/next-release/bugfix-7029c1d5-212c-48ac-9513-38f0beca8fa8.json
new file mode 100644
index 00000000000..f74a5086d47
--- /dev/null
+++ b/.changes/next-release/bugfix-7029c1d5-212c-48ac-9513-38f0beca8fa8.json
@@ -0,0 +1,4 @@
+{
+  "type" : "bugfix",
+  "description" : "Fix unsupported files being shown in file picker when selecting images for adding image context in Windows"
+}
\ No newline at end of file
diff --git a/plugins/amazonq/shared/jetbrains-community/src-242/software/aws/toolkits/jetbrains/services/amazonq/lsp/util/FileChooserFilters.kt b/plugins/amazonq/shared/jetbrains-community/src-242/software/aws/toolkits/jetbrains/services/amazonq/lsp/util/FileChooserFilters.kt
new file mode 100644
index 00000000000..ea9e6a355ce
--- /dev/null
+++ b/plugins/amazonq/shared/jetbrains-community/src-242/software/aws/toolkits/jetbrains/services/amazonq/lsp/util/FileChooserFilters.kt
@@ -0,0 +1,29 @@
+// Copyright 2025 Amazon.com, Inc. or its affiliates. All Rights Reserved.
+// SPDX-License-Identifier: Apache-2.0
+
+package software.aws.toolkits.jetbrains.services.amazonq.lsp.util
+
+import com.intellij.openapi.fileChooser.FileChooserDescriptor
+
+/**
+ * Applies file extension filtering to the given FileChooserDescriptor for IntelliJ Platform versions before 2024.3 (baseline < 243).
+ * Uses withFileFilter method which provides filtering functionality but doesn't visually filter
+ * files in the chooser dialog.
+ *
+ * @param descriptor The FileChooserDescriptor to apply filtering to
+ * @param filterName The display name for the filter (e.g., "Images") - unused in this version
+ * @param allowedExtensions Set of allowed file extensions (e.g., "jpg", "png")
+ * @return The modified FileChooserDescriptor
+ */
+fun applyExtensionFilter(
+    descriptor: FileChooserDescriptor,
+    @Suppress("UNUSED_PARAMETER") filterName: String,
+    allowedExtensions: Set<String>,
+): FileChooserDescriptor = descriptor.withFileFilter { virtualFile ->
+    if (virtualFile.isDirectory) {
+        true // Always allow directories for navigation
+    } else {
+        val extension = virtualFile.extension?.lowercase()
+        extension != null && allowedExtensions.contains(extension)
+    }
+}
diff --git a/plugins/amazonq/shared/jetbrains-community/src-243+/software/aws/toolkits/jetbrains/services/amazonq/lsp/util/FileChooserFilters.kt b/plugins/amazonq/shared/jetbrains-community/src-243+/software/aws/toolkits/jetbrains/services/amazonq/lsp/util/FileChooserFilters.kt
new file mode 100644
index 00000000000..bf60e987ebc
--- /dev/null
+++ b/plugins/amazonq/shared/jetbrains-community/src-243+/software/aws/toolkits/jetbrains/services/amazonq/lsp/util/FileChooserFilters.kt
@@ -0,0 +1,22 @@
+// Copyright 2025 Amazon.com, Inc. or its affiliates. All Rights Reserved.
+// SPDX-License-Identifier: Apache-2.0
+
+package software.aws.toolkits.jetbrains.services.amazonq.lsp.util
+
+import com.intellij.openapi.fileChooser.FileChooserDescriptor
+
+/**
+ * Applies file extension filtering to the given FileChooserDescriptor for IntelliJ Platform versions 2024.3+ (baseline >= 243).
+ * Uses withExtensionFilter method which provides both filtering functionality and visual
+ * filtering in the chooser dialog.
+ *
+ * @param descriptor The FileChooserDescriptor to apply filtering to
+ * @param filterName The display name for the filter (e.g., "Images")
+ * @param allowedExtensions Set of allowed file extensions (e.g., "jpg", "png")
+ * @return The modified FileChooserDescriptor
+ */
+fun applyExtensionFilter(
+    descriptor: FileChooserDescriptor,
+    filterName: String,
+    allowedExtensions: Set<String>,
+): FileChooserDescriptor = descriptor.withExtensionFilter(filterName, *allowedExtensions.toTypedArray())
diff --git a/plugins/amazonq/shared/jetbrains-community/src/software/aws/toolkits/jetbrains/services/amazonq/lsp/AmazonQLanguageClientImpl.kt b/plugins/amazonq/shared/jetbrains-community/src/software/aws/toolkits/jetbrains/services/amazonq/lsp/AmazonQLanguageClientImpl.kt
index 4b105142484..47d490cb93d 100644
--- a/plugins/amazonq/shared/jetbrains-community/src/software/aws/toolkits/jetbrains/services/amazonq/lsp/AmazonQLanguageClientImpl.kt
+++ b/plugins/amazonq/shared/jetbrains-community/src/software/aws/toolkits/jetbrains/services/amazonq/lsp/AmazonQLanguageClientImpl.kt
@@ -66,6 +66,7 @@ import software.aws.toolkits.jetbrains.services.amazonq.lsp.model.aws.chat.ShowS
 import software.aws.toolkits.jetbrains.services.amazonq.lsp.model.aws.credentials.ConnectionMetadata
 import software.aws.toolkits.jetbrains.services.amazonq.lsp.util.LspEditorUtil
 import software.aws.toolkits.jetbrains.services.amazonq.lsp.util.TelemetryParsingUtil
+import software.aws.toolkits.jetbrains.services.amazonq.lsp.util.applyExtensionFilter
 import software.aws.toolkits.jetbrains.services.codewhisperer.customization.CodeWhispererModelConfigurator
 import software.aws.toolkits.jetbrains.services.telemetry.TelemetryService
 import software.aws.toolkits.jetbrains.settings.CodeWhispererSettings
@@ -311,15 +312,7 @@ class AmazonQLanguageClientImpl(private val project: Project) : AmazonQLanguageC
                     if (params.filters.isNotEmpty() && !params.canSelectFolders) {
                         // Create a combined list of all allowed extensions
                         val allowedExtensions = params.filters.values.flatten().toSet()
-
-                        withFileFilter { virtualFile ->
-                            if (virtualFile.isDirectory) {
-                                true // Always allow directories for navigation
-                            } else {
-                                val extension = virtualFile.extension?.lowercase()
-                                extension != null && allowedExtensions.contains(extension)
-                            }
-                        }
+                        applyExtensionFilter(this, "Images", allowedExtensions)
                     }
                 }