diff --git a/packages/browser-repl/package.json b/packages/browser-repl/package.json
index bad4a20162..1256cdd2a2 100644
--- a/packages/browser-repl/package.json
+++ b/packages/browser-repl/package.json
@@ -36,6 +36,7 @@
     "@leafygreen-ui/palette": "^2.0.0",
     "@leafygreen-ui/syntax": "^2.2.0",
     "@mongosh/browser-runtime-core": "0.0.0-dev.0",
+    "@mongosh/errors": "0.0.0-dev.0",
     "@mongosh/history": "0.0.0-dev.0",
     "@mongosh/i18n": "0.0.0-dev.0",
     "@mongosh/node-runtime-worker-thread": "0.0.0-dev.0",
diff --git a/packages/browser-repl/src/components/types/error-output.tsx b/packages/browser-repl/src/components/types/error-output.tsx
index 7b43ce735c..5aae48e893 100644
--- a/packages/browser-repl/src/components/types/error-output.tsx
+++ b/packages/browser-repl/src/components/types/error-output.tsx
@@ -1,5 +1,6 @@
 import React, { Component } from 'react';
 import PropTypes from 'prop-types';
+import { isShouldReportAsBugError } from '@mongosh/errors';
 
 import { SimpleTypeOutput } from './simple-type-output';
 import { Expandable } from '../utils/expandable';
@@ -26,6 +27,16 @@ export class ErrorOutput extends Component<ErrorOutputProps> {
     return this.props.value.stack.split('\n').slice(1).join('\n');
   }
 
+  formatErrorBugReportInfo(): JSX.Element | undefined {
+    if (isShouldReportAsBugError(this.props.value)) {
+      return (<div>
+        This is an error inside mongosh.
+        Please <a href="https://jira.mongodb.org/projects/MONGOSH/issues" target="_blank">file a bug report for the MONGOSH project</a>.
+      </div>);
+    }
+    return undefined;
+  }
+
   formatErrorInfo(): JSX.Element | undefined {
     if (this.props.value.errInfo) {
       return (<div>
@@ -50,6 +61,7 @@ export class ErrorOutput extends Component<ErrorOutputProps> {
     return (<div>
       {this.renderCollapsed(toggle)}
       <div>
+        {this.formatErrorBugReportInfo()}
         {this.formatErrorInfo()}
         {this.formatErrorResult()}
         <pre>{this.formatStack()}</pre>
diff --git a/packages/cli-repl/src/cli-repl.ts b/packages/cli-repl/src/cli-repl.ts
index 6b5853675b..c79174aad4 100644
--- a/packages/cli-repl/src/cli-repl.ts
+++ b/packages/cli-repl/src/cli-repl.ts
@@ -276,18 +276,21 @@ class CliRepl {
     }
   }
 
+  get logFilePath(): string {
+    return this.shellHomeDirectory.localPath(`${this.logId}_log`);
+  }
+
   /**
    * Open a writable stream for the current log file.
    */
   async openLogStream(): Promise<Writable> {
-    const path = this.shellHomeDirectory.localPath(`${this.logId}_log`);
     await this.cleanupOldLogfiles();
     try {
-      const stream = createWriteStream(path, { mode: 0o600 });
+      const stream = createWriteStream(this.logFilePath, { mode: 0o600 });
       await once(stream, 'ready');
       return stream;
     } catch (err) {
-      this.warnAboutInaccessibleFile(err, path);
+      this.warnAboutInaccessibleFile(err, this.logFilePath);
       return new Writable({
         write(chunk, enc, cb) {
           // Just ignore log data if there was an error.
@@ -492,6 +495,10 @@ class CliRepl {
       throw e;
     }
   }
+
+  bugReportErrorMessageInfo(): string {
+    return `Please include the log file for this session (${this.logFilePath}).`;
+  }
 }
 
 export default CliRepl;
diff --git a/packages/cli-repl/src/format-output.ts b/packages/cli-repl/src/format-output.ts
index cc2c6f4362..8e84822765 100644
--- a/packages/cli-repl/src/format-output.ts
+++ b/packages/cli-repl/src/format-output.ts
@@ -7,6 +7,7 @@ import util from 'util';
 import stripAnsi from 'strip-ansi';
 import clr from './clr';
 import { HelpProperties, CollectionNamesWithTypes } from '@mongosh/shell-api';
+import { isShouldReportAsBugError } from '@mongosh/errors';
 
 type EvaluationResult = {
   value: any;
@@ -20,6 +21,7 @@ type FormatOptions = {
   maxArrayLength?: number;
   maxStringLength?: number;
   showStackTraces?: boolean;
+  bugReportErrorMessageInfo?: string;
 };
 
 /**
@@ -178,6 +180,12 @@ export function formatError(error: Error, options: FormatOptions): string {
   let result = '';
   if (error.name) result += `\r${clr(error.name, ['bold', 'red'], options)}: `;
   if (error.message) result += error.message;
+  if (isShouldReportAsBugError(error)) {
+    result += '\nThis is an error inside mongosh. Please file a bug report for the MONGOSH project here: https://jira.mongodb.org/projects/MONGOSH/issues.';
+    if (options.bugReportErrorMessageInfo) {
+      result += `\n${options.bugReportErrorMessageInfo}`;
+    }
+  }
   if (error.name === 'SyntaxError') {
     if (!options.colors) {
       // Babel applies syntax highlighting to its errors by default.
diff --git a/packages/cli-repl/src/mongosh-repl.ts b/packages/cli-repl/src/mongosh-repl.ts
index ec37cb424d..f7526ce5d5 100644
--- a/packages/cli-repl/src/mongosh-repl.ts
+++ b/packages/cli-repl/src/mongosh-repl.ts
@@ -31,6 +31,7 @@ export type MongoshIOProvider = Omit<ConfigProvider<CliUserConfig>, 'validateCon
   exit(code?: number): Promise<never>;
   readFileUTF8(filename: string): Promise<{ contents: string, absolutePath: string }>;
   startMongocryptd(): Promise<AutoEncryptionOptions['extraOptions']>;
+  bugReportErrorMessageInfo?(): string | undefined;
 };
 
 export type MongoshNodeReplOptions = {
@@ -599,14 +600,15 @@ class MongoshNodeRepl implements EvaluationListener {
     return clr(text, style, this.getFormatOptions());
   }
 
-  getFormatOptions(): { colors: boolean, compact: number | boolean, depth: number, showStackTraces: boolean } {
+  getFormatOptions(): { colors: boolean, compact: number | boolean, depth: number, showStackTraces: boolean, bugReportErrorMessageInfo?: string } {
     const output = this.output as WriteStream;
     return {
       colors: this._runtimeState?.repl?.useColors ??
         (output.isTTY && output.getColorDepth() > 1),
       compact: this.inspectCompact,
       depth: this.inspectDepth,
-      showStackTraces: this.showStackTraces
+      showStackTraces: this.showStackTraces,
+      bugReportErrorMessageInfo: this.ioProvider.bugReportErrorMessageInfo?.()
     };
   }
 
diff --git a/packages/cli-repl/test/e2e.spec.ts b/packages/cli-repl/test/e2e.spec.ts
index 6f3a5ebb8a..e30280ef8c 100644
--- a/packages/cli-repl/test/e2e.spec.ts
+++ b/packages/cli-repl/test/e2e.spec.ts
@@ -124,6 +124,12 @@ describe('e2e', function() {
       shell.writeInputLine('process.exitCode = 42; quit()');
       expect(await onExit).to.equal(42);
     });
+    it('decorates internal errors with bug reporting information', async() => {
+      const err = await shell.executeLine('throw Object.assign(new Error("foo"), { code: "COMMON-90001" })');
+      expect(err).to.match(/^Error: foo$/m);
+      expect(err).to.match(/^This is an error inside mongosh\. Please file a bug report for the MONGOSH project here: https:\/\/jira.mongodb.org\/projects\/MONGOSH\/issues\.$/m);
+      expect(err).to.match(/^Please include the log file for this session \(.+[/\\][a-f0-9]{24}_log\)\.$/m);
+    });
   });
   describe('set db', () => {
     for (const { mode, dbname, dbnameUri } of [
diff --git a/packages/errors/src/index.spec.ts b/packages/errors/src/index.spec.ts
index 5a4ce8eca5..c842c86e39 100644
--- a/packages/errors/src/index.spec.ts
+++ b/packages/errors/src/index.spec.ts
@@ -26,7 +26,7 @@ describe('errors', () => {
     const error = new MongoshInternalError('Something went wrong.');
     expect(error).to.be.instanceOf(MongoshBaseError);
     expect(error.name).to.be.equal('MongoshInternalError');
-    expect(error.message).to.be.equal('[COMMON-90001] Something went wrong.\nThis is an error inside mongosh. Please file a bug report for the MONGOSH project here: https://jira.mongodb.org/projects/MONGOSH/issues.');
+    expect(error.message).to.be.equal('[COMMON-90001] Something went wrong.');
     expect(error.code).to.be.equal(CommonErrors.UnexpectedInternalError);
     expect(error.scope).to.be.equal('COMMON');
   });
diff --git a/packages/errors/src/index.ts b/packages/errors/src/index.ts
index d03b564779..18bcdfb87b 100644
--- a/packages/errors/src/index.ts
+++ b/packages/errors/src/index.ts
@@ -8,6 +8,10 @@ function getScopeFromErrorCode(code: string | null | undefined): string | undefi
   return !match ? undefined : match[1];
 }
 
+function isShouldReportAsBugError(err: Error & { code?: string }): boolean {
+  return err?.code === CommonErrors.UnexpectedInternalError;
+}
+
 abstract class MongoshBaseError extends Error {
   readonly code: string | undefined;
   readonly scope: string | undefined;
@@ -32,8 +36,7 @@ class MongoshInternalError extends MongoshBaseError {
   constructor(message: string, metadata?: Object) {
     super(
       'MongoshInternalError',
-      `${message}
-This is an error inside mongosh. Please file a bug report for the MONGOSH project here: https://jira.mongodb.org/projects/MONGOSH/issues.`,
+      message,
       CommonErrors.UnexpectedInternalError,
       metadata
     );
@@ -82,6 +85,7 @@ class MongoshCommandFailed extends MongoshBaseError {
 
 export {
   getScopeFromErrorCode,
+  isShouldReportAsBugError,
   MongoshBaseError,
   MongoshWarning,
   MongoshRuntimeError,