diff --git a/emain/emain-platform.ts b/emain/emain-platform.ts
index 714316b93e..86b49a07e2 100644
--- a/emain/emain-platform.ts
+++ b/emain/emain-platform.ts
@@ -193,6 +193,9 @@ ipcMain.on("get-data-dir", (event) => {
 ipcMain.on("get-config-dir", (event) => {
     event.returnValue = getWaveConfigDir();
 });
+ipcMain.on("get-home-dir", (event) => {
+    event.returnValue = app.getPath("home");
+});
 
 /**
  * Gets the value of the XDG_CURRENT_DESKTOP environment variable. If ORIGINAL_XDG_CURRENT_DESKTOP is set, it will be returned instead.
diff --git a/emain/preload.ts b/emain/preload.ts
index bdde36096f..cc9af57031 100644
--- a/emain/preload.ts
+++ b/emain/preload.ts
@@ -12,6 +12,7 @@ contextBridge.exposeInMainWorld("api", {
     getHostName: () => ipcRenderer.sendSync("get-host-name"),
     getDataDir: () => ipcRenderer.sendSync("get-data-dir"),
     getConfigDir: () => ipcRenderer.sendSync("get-config-dir"),
+    getHomeDir: () => ipcRenderer.sendSync("get-home-dir"),
     getAboutModalDetails: () => ipcRenderer.sendSync("get-about-modal-details"),
     getDocsiteUrl: () => ipcRenderer.sendSync("get-docsite-url"),
     getWebviewPreload: () => ipcRenderer.sendSync("get-webview-preload"),
diff --git a/frontend/app/view/codeeditor/schemaendpoints.ts b/frontend/app/view/codeeditor/schemaendpoints.ts
index dd6068c477..5056f7121e 100644
--- a/frontend/app/view/codeeditor/schemaendpoints.ts
+++ b/frontend/app/view/codeeditor/schemaendpoints.ts
@@ -10,11 +10,34 @@ type EndpointInfo = {
     schema: object;
 };
 
+function prependWildcard(path: string): string {
+    return path.startsWith("/") ? `*${path}` : `*/${path}`;
+}
+
+function convertToTildePath(absolutePath: string): string {
+    const homeDir = getApi().getHomeDir();
+    if (absolutePath.startsWith(homeDir)) {
+        return "~" + absolutePath.slice(homeDir.length);
+    }
+    return absolutePath;
+}
+
+function makeConfigPathMatches(suffix: string): Array<string> {
+    const configPath = `${getApi().getConfigDir()}${suffix}`;
+    const tildePath = convertToTildePath(configPath);
+    const paths = [configPath, prependWildcard(configPath)];
+    if (tildePath !== configPath) {
+        paths.push(tildePath);
+        paths.push(prependWildcard(tildePath));
+    }
+    return paths;
+}
+
 const allFilepaths: Map<string, Array<string>> = new Map();
-allFilepaths.set(`${getWebServerEndpoint()}/schema/settings.json`, [`${getApi().getConfigDir()}/settings.json`]);
-allFilepaths.set(`${getWebServerEndpoint()}/schema/connections.json`, [`${getApi().getConfigDir()}/connections.json`]);
-allFilepaths.set(`${getWebServerEndpoint()}/schema/aipresets.json`, [`${getApi().getConfigDir()}/presets/ai.json`]);
-allFilepaths.set(`${getWebServerEndpoint()}/schema/widgets.json`, [`${getApi().getConfigDir()}/widgets.json`]);
+allFilepaths.set(`${getWebServerEndpoint()}/schema/settings.json`, makeConfigPathMatches("/settings.json"));
+allFilepaths.set(`${getWebServerEndpoint()}/schema/connections.json`, makeConfigPathMatches("/connections.json"));
+allFilepaths.set(`${getWebServerEndpoint()}/schema/aipresets.json`, makeConfigPathMatches("/presets/ai.json"));
+allFilepaths.set(`${getWebServerEndpoint()}/schema/widgets.json`, makeConfigPathMatches("/widgets.json"));
 
 async function getSchemaEndpointInfo(endpoint: string): Promise<EndpointInfo> {
     let schema: Object;
diff --git a/frontend/types/custom.d.ts b/frontend/types/custom.d.ts
index 3c5c26650a..23c51a9b95 100644
--- a/frontend/types/custom.d.ts
+++ b/frontend/types/custom.d.ts
@@ -83,6 +83,7 @@ declare global {
         getHostName: () => string; // get-host-name
         getDataDir: () => string; // get-data-dir
         getConfigDir: () => string; // get-config-dir
+        getHomeDir: () => string; // get-home-dir
         getWebviewPreload: () => string; // get-webview-preload
         getAboutModalDetails: () => AboutModalDetails; // get-about-modal-details
         getDocsiteUrl: () => string; // get-docsite-url
diff --git a/pkg/aiusechat/openai/openai-convertmessage.go b/pkg/aiusechat/openai/openai-convertmessage.go
index 78f91e7b5d..31cbe1fd04 100644
--- a/pkg/aiusechat/openai/openai-convertmessage.go
+++ b/pkg/aiusechat/openai/openai-convertmessage.go
@@ -6,7 +6,9 @@ package openai
 import (
 	"bytes"
 	"context"
+	"crypto/sha256"
 	"encoding/base64"
+	"encoding/hex"
 	"encoding/json"
 	"errors"
 	"fmt"
@@ -58,6 +60,16 @@ func extractXmlAttribute(tag, attrName string) (string, bool) {
 	return value, true
 }
 
+// generateDeterministicSuffix creates an 8-character hash from input strings
+func generateDeterministicSuffix(inputs ...string) string {
+	hasher := sha256.New()
+	for _, input := range inputs {
+		hasher.Write([]byte(input))
+	}
+	hash := hasher.Sum(nil)
+	return hex.EncodeToString(hash)[:8]
+}
+
 // ---------- OpenAI Request Types ----------
 
 type StreamOptionsType struct {
@@ -388,8 +400,8 @@ func convertFileAIMessagePart(part uctypes.AIMessagePart) (*OpenAIMessageContent
 		encodedFileName := strings.ReplaceAll(fileName, `"`, "&quot;")
 		quotedFileName := strconv.Quote(encodedFileName)
 
-		randomSuffix := uuid.New().String()[0:8]
-		formattedText := fmt.Sprintf("<AttachedTextFile_%s file_name=%s>\n%s\n</AttachedTextFile_%s>", randomSuffix, quotedFileName, textContent, randomSuffix)
+		deterministicSuffix := generateDeterministicSuffix(textContent, fileName)
+		formattedText := fmt.Sprintf("<AttachedTextFile_%s file_name=%s>\n%s\n</AttachedTextFile_%s>", deterministicSuffix, quotedFileName, textContent, deterministicSuffix)
 
 		return &OpenAIMessageContent{
 			Type: "input_text",
@@ -412,8 +424,8 @@ func convertFileAIMessagePart(part uctypes.AIMessagePart) (*OpenAIMessageContent
 		encodedDirName := strings.ReplaceAll(directoryName, `"`, "&quot;")
 		quotedDirName := strconv.Quote(encodedDirName)
 
-		randomSuffix := uuid.New().String()[0:8]
-		formattedText := fmt.Sprintf("<AttachedDirectoryListing_%s directory_name=%s>\n%s\n</AttachedDirectoryListing_%s>", randomSuffix, quotedDirName, jsonContent, randomSuffix)
+		deterministicSuffix := generateDeterministicSuffix(jsonContent, directoryName)
+		formattedText := fmt.Sprintf("<AttachedDirectoryListing_%s directory_name=%s>\n%s\n</AttachedDirectoryListing_%s>", deterministicSuffix, quotedDirName, jsonContent, deterministicSuffix)
 
 		return &OpenAIMessageContent{
 			Type: "input_text",