diff --git a/core/protocol/core.ts b/core/protocol/core.ts
index 28e617f798f..f23666165bf 100644
--- a/core/protocol/core.ts
+++ b/core/protocol/core.ts
@@ -307,7 +307,11 @@ export type ToCoreFromIdeOrWebviewProtocol = {
   "auth/getAuthUrl": [{ useOnboarding: boolean }, { url: string }];
   "tools/call": [
     { toolCall: ToolCall },
-    { contextItems: ContextItem[]; errorMessage?: string },
+    {
+      contextItems: ContextItem[];
+      errorMessage?: string;
+      errorReason?: ContinueErrorReason;
+    },
   ];
   "tools/evaluatePolicy": [
     { toolName: string; basePolicy: ToolPolicy; args: Record<string, unknown> },
diff --git a/core/tools/callTool.ts b/core/tools/callTool.ts
index faec8a94b8c..8d695e1e192 100644
--- a/core/tools/callTool.ts
+++ b/core/tools/callTool.ts
@@ -1,6 +1,7 @@
 import { CallToolResultSchema } from "@modelcontextprotocol/sdk/types.js";
 import { ContextItem, Tool, ToolCall, ToolExtras } from "..";
 import { MCPManagerSingleton } from "../context/mcp/MCPManagerSingleton";
+import { ContinueError, ContinueErrorReason } from "../util/errors";
 import { canParseUrl } from "../util/url";
 import { BuiltInToolNames } from "./builtIn";
 
@@ -197,6 +198,7 @@ export async function callTool(
 ): Promise<{
   contextItems: ContextItem[];
   errorMessage: string | undefined;
+  errorReason?: ContinueErrorReason;
 }> {
   try {
     const args = safeParseToolCallArgs(toolCall);
@@ -214,12 +216,19 @@ export async function callTool(
     };
   } catch (e) {
     let errorMessage = `${e}`;
-    if (e instanceof Error) {
+    let errorReason: ContinueErrorReason | undefined;
+
+    if (e instanceof ContinueError) {
+      errorMessage = e.message;
+      errorReason = e.reason;
+    } else if (e instanceof Error) {
       errorMessage = e.message;
     }
+
     return {
       contextItems: [],
       errorMessage,
+      errorReason,
     };
   }
 }
diff --git a/core/tools/implementations/createNewFile.ts b/core/tools/implementations/createNewFile.ts
index 0677e7dcd0f..dca307d99d6 100644
--- a/core/tools/implementations/createNewFile.ts
+++ b/core/tools/implementations/createNewFile.ts
@@ -3,6 +3,7 @@ import { inferResolvedUriFromRelativePath } from "../../util/ideUtils";
 import { ToolImpl } from ".";
 import { getCleanUriPath, getUriPathBasename } from "../../util/uri";
 import { getStringArg } from "../parseArgs";
+import { ContinueError, ContinueErrorReason } from "../../util/errors";
 
 export const createNewFileImpl: ToolImpl = async (args, extras) => {
   const filepath = getStringArg(args, "filepath");
@@ -15,7 +16,8 @@ export const createNewFileImpl: ToolImpl = async (args, extras) => {
   if (resolvedFileUri) {
     const exists = await extras.ide.fileExists(resolvedFileUri);
     if (exists) {
-      throw new Error(
+      throw new ContinueError(
+        ContinueErrorReason.FileAlreadyExists,
         `File ${filepath} already exists. Use the edit tool to edit this file`,
       );
     }
@@ -37,6 +39,9 @@ export const createNewFileImpl: ToolImpl = async (args, extras) => {
       },
     ];
   } else {
-    throw new Error("Failed to resolve path");
+    throw new ContinueError(
+      ContinueErrorReason.PathResolutionFailed,
+      "Failed to resolve path",
+    );
   }
 };
diff --git a/core/tools/implementations/grepSearch.ts b/core/tools/implementations/grepSearch.ts
index 727b5c560bf..69ccf6aacc3 100644
--- a/core/tools/implementations/grepSearch.ts
+++ b/core/tools/implementations/grepSearch.ts
@@ -1,5 +1,6 @@
 import { ToolImpl } from ".";
 import { ContextItem } from "../..";
+import { ContinueError, ContinueErrorReason } from "../../util/errors";
 import { formatGrepSearchResults } from "../../util/grepSearch";
 import { prepareQueryForRipgrep } from "../../util/regexValidator";
 import { getStringArg } from "../parseArgs";
@@ -63,7 +64,10 @@ export const grepSearchImpl: ToolImpl = async (args, extras) => {
       ];
     }
 
-    throw error;
+    throw new ContinueError(
+      ContinueErrorReason.SearchExecutionFailed,
+      errorMessage,
+    );
   }
 
   const { formatted, numResults, truncated } = formatGrepSearchResults(
diff --git a/core/tools/implementations/lsTool.ts b/core/tools/implementations/lsTool.ts
index 67122f082be..67e0bb1718d 100644
--- a/core/tools/implementations/lsTool.ts
+++ b/core/tools/implementations/lsTool.ts
@@ -3,6 +3,7 @@ import ignore from "ignore";
 import { ToolImpl } from ".";
 import { walkDir } from "../../indexing/walkDir";
 import { resolveRelativePathInDir } from "../../util/ideUtils";
+import { ContinueError, ContinueErrorReason } from "../../util/errors";
 
 export function resolveLsToolDirPath(dirPath: string | undefined) {
   if (!dirPath || dirPath === ".") {
@@ -20,7 +21,8 @@ export const lsToolImpl: ToolImpl = async (args, extras) => {
   const dirPath = resolveLsToolDirPath(args?.dirPath);
   const uri = await resolveRelativePathInDir(dirPath, extras.ide);
   if (!uri) {
-    throw new Error(
+    throw new ContinueError(
+      ContinueErrorReason.DirectoryNotFound,
       `Directory ${args.dirPath} not found. Make sure to use forward-slash paths`,
     );
   }
diff --git a/core/tools/implementations/readFile.ts b/core/tools/implementations/readFile.ts
index afa6495ad08..8daee746212 100644
--- a/core/tools/implementations/readFile.ts
+++ b/core/tools/implementations/readFile.ts
@@ -5,6 +5,7 @@ import { ToolImpl } from ".";
 import { throwIfFileIsSecurityConcern } from "../../indexing/ignore";
 import { getStringArg } from "../parseArgs";
 import { throwIfFileExceedsHalfOfContext } from "./readFileLimit";
+import { ContinueError, ContinueErrorReason } from "../../util/errors";
 
 export const readFileImpl: ToolImpl = async (args, extras) => {
   const filepath = getStringArg(args, "filepath");
@@ -12,7 +13,8 @@ export const readFileImpl: ToolImpl = async (args, extras) => {
 
   const firstUriMatch = await resolveRelativePathInDir(filepath, extras.ide);
   if (!firstUriMatch) {
-    throw new Error(
+    throw new ContinueError(
+      ContinueErrorReason.FileNotFound,
       `File "${filepath}" does not exist. You might want to check the path and try again.`,
     );
   }
diff --git a/core/tools/implementations/readFileLimit.ts b/core/tools/implementations/readFileLimit.ts
index e2af14d5665..48f4b9f860b 100644
--- a/core/tools/implementations/readFileLimit.ts
+++ b/core/tools/implementations/readFileLimit.ts
@@ -1,5 +1,6 @@
 import { ILLM } from "../..";
 import { countTokensAsync } from "../../llm/countTokens";
+import { ContinueError, ContinueErrorReason } from "../../util/errors";
 
 export async function throwIfFileExceedsHalfOfContext(
   filepath: string,
@@ -10,7 +11,8 @@ export async function throwIfFileExceedsHalfOfContext(
     const tokens = await countTokensAsync(content, model.title);
     const tokenLimit = model.contextLength / 2;
     if (tokens > tokenLimit) {
-      throw new Error(
+      throw new ContinueError(
+        ContinueErrorReason.FileTooLarge,
         `File ${filepath} is too large (${tokens} tokens vs ${tokenLimit} token limit). Try another approach`,
       );
     }
diff --git a/core/tools/implementations/readFileRange.ts b/core/tools/implementations/readFileRange.ts
index c313f4bff14..0ff97d18991 100644
--- a/core/tools/implementations/readFileRange.ts
+++ b/core/tools/implementations/readFileRange.ts
@@ -4,6 +4,7 @@ import { getUriPathBasename } from "../../util/uri";
 import { ToolImpl } from ".";
 import { getNumberArg, getStringArg } from "../parseArgs";
 import { throwIfFileExceedsHalfOfContext } from "./readFileLimit";
+import { ContinueError, ContinueErrorReason } from "../../util/errors";
 
 export const readFileRangeImpl: ToolImpl = async (args, extras) => {
   const filepath = getStringArg(args, "filepath");
@@ -12,24 +13,28 @@ export const readFileRangeImpl: ToolImpl = async (args, extras) => {
 
   // Validate that line numbers are positive integers
   if (startLine < 1) {
-    throw new Error(
+    throw new ContinueError(
+      ContinueErrorReason.InvalidLineNumber,
       "startLine must be 1 or greater. Negative line numbers are not supported - use the terminal tool with 'tail' command for reading from file end.",
     );
   }
   if (endLine < 1) {
-    throw new Error(
+    throw new ContinueError(
+      ContinueErrorReason.InvalidLineNumber,
       "endLine must be 1 or greater. Negative line numbers are not supported - use the terminal tool with 'tail' command for reading from file end.",
     );
   }
   if (endLine < startLine) {
-    throw new Error(
+    throw new ContinueError(
+      ContinueErrorReason.InvalidLineNumber,
       `endLine (${endLine}) must be greater than or equal to startLine (${startLine})`,
     );
   }
 
   const firstUriMatch = await resolveRelativePathInDir(filepath, extras.ide);
   if (!firstUriMatch) {
-    throw new Error(
+    throw new ContinueError(
+      ContinueErrorReason.FileNotFound,
       `File "${filepath}" does not exist. You might want to check the path and try again.`,
     );
   }
diff --git a/core/tools/implementations/requestRule.ts b/core/tools/implementations/requestRule.ts
index c5c312e7087..21ee86af852 100644
--- a/core/tools/implementations/requestRule.ts
+++ b/core/tools/implementations/requestRule.ts
@@ -1,4 +1,5 @@
 import { ToolImpl } from ".";
+import { ContinueError, ContinueErrorReason } from "../../util/errors";
 import { getStringArg } from "../parseArgs";
 
 export const requestRuleImpl: ToolImpl = async (args, extras) => {
@@ -8,7 +9,10 @@ export const requestRuleImpl: ToolImpl = async (args, extras) => {
   const rule = extras.config.rules.find((r) => r.name === name);
 
   if (!rule || !rule.sourceFile) {
-    throw new Error(`Rule with name "${name}" not found or has no file path`);
+    throw new ContinueError(
+      ContinueErrorReason.RuleNotFound,
+      `Rule with name "${name}" not found or has no file path`,
+    );
   }
 
   return [
diff --git a/core/tools/implementations/runTerminalCommand.ts b/core/tools/implementations/runTerminalCommand.ts
index cccf3353b18..15b1dc1bffb 100644
--- a/core/tools/implementations/runTerminalCommand.ts
+++ b/core/tools/implementations/runTerminalCommand.ts
@@ -2,6 +2,7 @@ import iconv from "iconv-lite";
 import childProcess from "node:child_process";
 import os from "node:os";
 import util from "node:util";
+import { ContinueError, ContinueErrorReason } from "../../util/errors";
 // Automatically decode the buffer according to the platform to avoid garbled Chinese
 function getDecodedOutput(data: Buffer): string {
   if (process.platform === "win32") {
@@ -337,7 +338,8 @@ export const runTerminalCommandImpl: ToolImpl = async (args, extras) => {
                 if (code === 0) {
                   resolve({ stdout, stderr });
                 } else {
-                  const error = new Error(
+                  const error = new ContinueError(
+                    ContinueErrorReason.CommandExecutionFailed,
                     `Command failed with exit code ${code}`,
                   );
                   (error as any).stderr = stderr;
diff --git a/core/tools/implementations/viewSubdirectory.ts b/core/tools/implementations/viewSubdirectory.ts
index b7897aae8a4..de546833852 100644
--- a/core/tools/implementations/viewSubdirectory.ts
+++ b/core/tools/implementations/viewSubdirectory.ts
@@ -2,6 +2,7 @@ import generateRepoMap from "../../util/generateRepoMap";
 import { resolveRelativePathInDir } from "../../util/ideUtils";
 
 import { ToolImpl } from ".";
+import { ContinueError, ContinueErrorReason } from "../../util/errors";
 import { getStringArg } from "../parseArgs";
 
 export const viewSubdirectoryImpl: ToolImpl = async (args: any, extras) => {
@@ -10,7 +11,10 @@ export const viewSubdirectoryImpl: ToolImpl = async (args: any, extras) => {
   const uri = await resolveRelativePathInDir(directory_path, extras.ide);
 
   if (!uri) {
-    throw new Error(`Directory path "${directory_path}" does not exist.`);
+    throw new ContinueError(
+      ContinueErrorReason.DirectoryNotFound,
+      `Directory path "${directory_path}" does not exist.`,
+    );
   }
 
   const repoMap = await generateRepoMap(extras.llm, extras.ide, {
diff --git a/core/util/errors.ts b/core/util/errors.ts
index 4c6cfb16d32..69df7c81423 100644
--- a/core/util/errors.ts
+++ b/core/util/errors.ts
@@ -47,6 +47,20 @@ export enum ContinueErrorReason {
   FileWriteError = "file_write_error",
   FileIsSecurityConcern = "file_is_security_concern",
   ParentDirectoryNotFound = "parent_directory_not_found",
+  FileTooLarge = "file_too_large",
+  PathResolutionFailed = "path_resolution_failed",
+  InvalidLineNumber = "invalid_line_number",
+  DirectoryNotFound = "directory_not_found",
+
+  // Terminal/Command execution
+  CommandExecutionFailed = "command_execution_failed",
+  CommandNotAvailableInRemote = "command_not_available_in_remote",
+
+  // Search
+  SearchExecutionFailed = "search_execution_failed",
+
+  // Rules
+  RuleNotFound = "rule_not_found",
 
   // Other
   Unspecified = "unspecified", // I.e. a known error but no specific code for it
diff --git a/extensions/cli/src/telemetry/telemetryService.ts b/extensions/cli/src/telemetry/telemetryService.ts
index f8121129850..910c82f59ed 100644
--- a/extensions/cli/src/telemetry/telemetryService.ts
+++ b/extensions/cli/src/telemetry/telemetryService.ts
@@ -17,6 +17,7 @@ import {
 } from "@opentelemetry/semantic-conventions";
 import { v4 as uuidv4 } from "uuid";
 
+import { ContinueErrorReason } from "../../../../core/util/errors.js";
 import { isHeadlessMode } from "../util/cli.js";
 import { isContinueRemoteAgent, isGitHubActions } from "../util/git.js";
 import { logger } from "../util/logger.js";
@@ -498,7 +499,7 @@ class TelemetryService {
     success: boolean;
     durationMs: number;
     error?: string;
-    errorReason?: string;
+    errorReason?: ContinueErrorReason;
     decision?: "accept" | "reject";
     source?: string;
     toolParameters?: string;
diff --git a/gui/src/redux/thunks/callToolById.ts b/gui/src/redux/thunks/callToolById.ts
index 9c9689b87aa..d0da3465fca 100644
--- a/gui/src/redux/thunks/callToolById.ts
+++ b/gui/src/redux/thunks/callToolById.ts
@@ -94,7 +94,7 @@ export const callToolById = createAsyncThunk<
       output = result.content.contextItems;
       error = result.content.errorMessage
         ? new ContinueError(
-            ContinueErrorReason.Unspecified,
+            result.content.errorReason || ContinueErrorReason.Unspecified,
             result.content.errorMessage,
           )
         : undefined;