diff --git a/packages/e2e-tests/test/e2e-analytics.spec.ts b/packages/e2e-tests/test/e2e-analytics.spec.ts
index e32bf1511..f214bda2d 100644
--- a/packages/e2e-tests/test/e2e-analytics.spec.ts
+++ b/packages/e2e-tests/test/e2e-analytics.spec.ts
@@ -46,7 +46,7 @@ describe('e2e Analytics Node', function () {
         );
         expect(helloIsWritablePrimary).to.contain('true');
       },
-      { timeout: 20_000 }
+      { timeout: 40_000 }
     );
   });
 
diff --git a/packages/e2e-tests/test/e2e-auth.spec.ts b/packages/e2e-tests/test/e2e-auth.spec.ts
index 70c7bc83b..379e37742 100644
--- a/packages/e2e-tests/test/e2e-auth.spec.ts
+++ b/packages/e2e-tests/test/e2e-auth.spec.ts
@@ -1,7 +1,6 @@
 import { expect } from 'chai';
 import type { Db, Document, MongoClientOptions } from 'mongodb';
 import { MongoClient } from 'mongodb';
-import { eventually } from '../../../testing/eventually';
 import type { TestShell } from './test-shell';
 import {
   skipIfApiStrict,
@@ -298,7 +297,7 @@ describe('Auth e2e', function () {
         it('dropAllUsers', async function () {
           await shell.executeLine(`use ${dbName}`);
           shell.writeInputLine('db.dropAllUsers()');
-          await eventually(() => {
+          await shell.eventually(() => {
             try {
               shell.assertContainsOutput('{ n: 2, ok: 1 }');
             } catch {
@@ -508,7 +507,7 @@ describe('Auth e2e', function () {
         it('dropAllRoles', async function () {
           await shell.executeLine(`use ${dbName}`);
           shell.writeInputLine('db.dropAllRoles()');
-          await eventually(() => {
+          await shell.eventually(() => {
             try {
               shell.assertContainsOutput('{ n: 2, ok: 1 }');
             } catch {
@@ -737,7 +736,7 @@ describe('Auth e2e', function () {
         it('throws if pwd is wrong', async function () {
           await shell.executeLine(`use ${dbName}`);
           shell.writeInputLine('db.auth("anna", "pwd2")');
-          await eventually(
+          await shell.eventually(
             () => {
               shell.assertContainsError('Authentication failed');
             },
@@ -752,7 +751,7 @@ describe('Auth e2e', function () {
           shell.writeInputLine(
             'db.auth({ user: "anna", pwd: "pwd2", mechanism: "not a mechanism"})'
           );
-          await eventually(
+          await shell.eventually(
             () => {
               expect(shell.output).to.match(
                 /MongoParseError: authMechanism one of .+, got not a mechanism/
@@ -1067,7 +1066,7 @@ describe('Auth e2e', function () {
             'SCRAM-SHA-1',
           ],
         });
-        await eventually(() => {
+        await shell.eventually(() => {
           expect(shell.output).to.match(
             /MongoServerError: Authentication failed|Unable to use SCRAM-SHA-1/
           );
@@ -1088,7 +1087,7 @@ describe('Auth e2e', function () {
             'SCRAM-SHA-256',
           ],
         });
-        await eventually(() => {
+        await shell.eventually(() => {
           expect(shell.output).to.match(
             /MongoServerError: Authentication failed|Unable to use SCRAM-SHA-256/
           );
diff --git a/packages/e2e-tests/test/e2e-direct.spec.ts b/packages/e2e-tests/test/e2e-direct.spec.ts
index 913cdfc7c..e97096117 100644
--- a/packages/e2e-tests/test/e2e-direct.spec.ts
+++ b/packages/e2e-tests/test/e2e-direct.spec.ts
@@ -64,12 +64,17 @@ describe('e2e direct connection', function () {
           `rs.initiate(${JSON.stringify(replSetConfig)})`
         );
         shell.assertContainsOutput('ok: 1');
-        await eventually(async () => {
-          await shell.executeLine('db.isMaster()');
-          shell.assertContainsOutput('ismaster: true');
-          shell.assertContainsOutput(`me: '${await rs0.hostport()}'`);
-          shell.assertContainsOutput(`setName: '${replSetId}'`);
-        });
+        await eventually(
+          async () => {
+            const output = await shell.executeLine('db.isMaster()');
+            expect(output).contains('ismaster: true');
+            expect(output).contains(`me: '${await rs0.hostport()}'`);
+            expect(output).contains(`setName: '${replSetId}'`);
+          },
+          {
+            timeout: 20_000,
+          }
+        );
 
         await shell.executeLine('use admin');
         await shell.executeLine(
@@ -204,7 +209,7 @@ describe('e2e direct connection', function () {
           await shell.waitForPrompt();
           shell.writeInput('db.testc');
           await tabtab(shell);
-          await eventually(() => {
+          await shell.eventually(() => {
             shell.assertContainsOutput('db.testcollection');
           });
         });
@@ -370,7 +375,7 @@ describe('e2e direct connection', function () {
           await shell.waitForPrompt();
           shell.writeInput('db.testc');
           await tabtab(shell);
-          await eventually(() => {
+          await shell.eventually(() => {
             shell.assertContainsOutput('db.testcollection');
           });
         });
diff --git a/packages/e2e-tests/test/e2e-editor.spec.ts b/packages/e2e-tests/test/e2e-editor.spec.ts
index ac6abb2fb..34563e93a 100644
--- a/packages/e2e-tests/test/e2e-editor.spec.ts
+++ b/packages/e2e-tests/test/e2e-editor.spec.ts
@@ -1,7 +1,6 @@
 import { expect } from 'chai';
 import path from 'path';
 import { promises as fs } from 'fs';
-import { eventually } from '../../../testing/eventually';
 import { TestShell } from './test-shell';
 import { ensureTestShellAfterHook } from './test-shell-context';
 import {
@@ -73,7 +72,7 @@ describe('external editor e2e', function () {
 
       expect(result).to.include('"editor" has been changed');
       shell.writeInputLine(shellOriginalInput);
-      await eventually(() => {
+      await shell.eventually(() => {
         shell.assertContainsOutput(shellModifiedInput);
       });
     });
@@ -97,7 +96,7 @@ describe('external editor e2e', function () {
 
       expect(result).to.include('"editor" has been changed');
       shell.writeInputLine(shellOriginalInput);
-      await eventually(() => {
+      await shell.eventually(() => {
         shell.assertContainsOutput(shellModifiedInput);
       });
     });
@@ -118,7 +117,7 @@ describe('external editor e2e', function () {
 
       expect(result).to.include('"editor" has been changed');
       shell.writeInputLine(shellOriginalInput);
-      await eventually(() => {
+      await shell.eventually(() => {
         shell.assertContainsOutput(shellModifiedInput);
       });
     });
@@ -145,7 +144,7 @@ describe('external editor e2e', function () {
 
       expect(result).to.include('"editor" has been changed');
       shell.writeInputLine(shellOriginalInput);
-      await eventually(() => {
+      await shell.eventually(() => {
         shell.assertContainsOutput(shellModifiedInput);
       });
     });
@@ -163,7 +162,7 @@ describe('external editor e2e', function () {
 
       expect(result).to.include('"editor" has been changed');
       shell.writeInputLine(shellOriginalInput);
-      await eventually(() => {
+      await shell.eventually(() => {
         shell.assertContainsError('failed with an exit code 1');
       });
     });
@@ -182,7 +181,7 @@ describe('external editor e2e', function () {
 
       expect(result).to.include('"editor" has been changed');
       shell.writeInputLine('edit');
-      await eventually(() => {
+      await shell.eventually(() => {
         shell.assertContainsOutput(output);
       });
     });
@@ -216,7 +215,7 @@ describe('external editor e2e', function () {
           "const name = 'I want to test a sequence of writeInputLine'"
         );
         shell.writeInputLine('edit name');
-        await eventually(() => {
+        await shell.eventually(() => {
           shell.assertContainsOutput(shellModifiedInput);
         });
       });
@@ -254,7 +253,7 @@ describe('external editor e2e', function () {
 
           expect(result).to.include('"editor" has been changed');
           shell.writeInputLine(shellOriginalInput);
-          await eventually(() => {
+          await shell.eventually(() => {
             shell.assertContainsOutput(shellModifiedInput);
           });
         });
@@ -279,7 +278,7 @@ describe('external editor e2e', function () {
 
           expect(result).to.include('"editor" has been changed');
           shell.writeInputLine(shellOriginalInput);
-          await eventually(() => {
+          await shell.eventually(() => {
             shell.assertContainsOutput(shellModifiedInput);
           });
         });
@@ -303,7 +302,7 @@ describe('external editor e2e', function () {
 
           expect(result).to.include('"editor" has been changed');
           shell.writeInputLine(shellOriginalInput);
-          await eventually(() => {
+          await shell.eventually(() => {
             shell.assertContainsOutput(shellModifiedInput);
           });
         });
diff --git a/packages/e2e-tests/test/e2e-snippet.spec.ts b/packages/e2e-tests/test/e2e-snippet.spec.ts
index 70b3c1914..a6cc6d85c 100644
--- a/packages/e2e-tests/test/e2e-snippet.spec.ts
+++ b/packages/e2e-tests/test/e2e-snippet.spec.ts
@@ -47,7 +47,7 @@ describe('snippet integration tests', function () {
 
   it('allows managing snippets', async function () {
     shell.writeInputLine('snippet install analyze-schema');
-    await eventually(
+    await shell.eventually(
       () => {
         shell.assertContainsOutput(
           'Installed new snippets analyze-schema. Do you want to load them now?'
@@ -77,7 +77,7 @@ describe('snippet integration tests', function () {
       return this.skip(); // https://jira.mongodb.org/browse/MONGOSH-746
     }
     shell.writeInput('snippet insta\t');
-    await eventually(() => {
+    await shell.eventually(() => {
       shell.assertContainsOutput('snippet install');
     });
   });
diff --git a/packages/e2e-tests/test/e2e.spec.ts b/packages/e2e-tests/test/e2e.spec.ts
index dc58693b9..1b4996816 100644
--- a/packages/e2e-tests/test/e2e.spec.ts
+++ b/packages/e2e-tests/test/e2e.spec.ts
@@ -165,7 +165,7 @@ describe('e2e', function () {
       shell.assertNoErrors();
 
       await shell.executeLine(',cat,\n');
-      await eventually(() => {
+      await shell.eventually(() => {
         expect(shell.rawOutput).to.match(
           /SyntaxError(\x1b\[.*m)+: Unexpected token/
         );
@@ -240,7 +240,7 @@ describe('e2e', function () {
       shell.writeInput('_+55\r\n');
       await promisify(setTimeout)(100);
       shell.writeInput('_+89\r\n');
-      await eventually(() => {
+      await shell.eventually(() => {
         shell.assertContainsOutput('233');
       });
     });
@@ -565,7 +565,7 @@ describe('e2e', function () {
 
     it('runs an unterminated function', async function () {
       shell.writeInputLine('function x () {');
-      await eventually(() => {
+      await shell.eventually(() => {
         shell.assertContainsOutput('...');
       });
       shell.assertNoErrors();
@@ -675,7 +675,7 @@ describe('e2e', function () {
         `load(${JSON.stringify(require.resolve('moment'))})`
       );
       shell.writeInputLine('print("loaded" + "scripts")');
-      await eventually(
+      await shell.eventually(
         () => {
           // Use eventually explicitly to get a bigger timeout, lodash is
           // quite “big” in terms of async rewriting
@@ -927,7 +927,7 @@ describe('e2e', function () {
             forceTerminal: true,
           });
 
-          await eventually(() => {
+          await shell.eventually(() => {
             if (shell.output.includes('Long sleep')) {
               return;
             }
@@ -936,7 +936,7 @@ describe('e2e', function () {
 
           shell.kill('SIGINT');
 
-          await eventually(() => {
+          await shell.eventually(() => {
             if (shell.output.includes('MongoshInterruptedError')) {
               return;
             }
@@ -1039,7 +1039,7 @@ describe('e2e', function () {
       db.coll1.insertOne({ foo: 89 });
       db.coll1.aggregate([{$group: {_id: null, total: {$sum: '$foo'}}}])
       `);
-      await eventually(() => {
+      await shell.eventually(() => {
         shell.assertContainsOutput('total: 144');
       });
     });
@@ -1052,7 +1052,7 @@ describe('e2e', function () {
       db.coll1.insertOne({ foo: 89 });
       db.coll1.aggregate([{$group: {_id: null, total: {$sum: '$foo'}}}])
       `);
-      await eventually(() => {
+      await shell.eventually(() => {
         shell.assertContainsOutput('total: 144');
       });
     });
@@ -1061,7 +1061,7 @@ describe('e2e', function () {
       createReadStream(
         path.resolve(__dirname, 'fixtures', 'exampleplayground.js')
       ).pipe(shell.process.stdin);
-      await eventually(() => {
+      await shell.eventually(() => {
         shell.assertContainsOutput("{ _id: 'xyz', totalSaleAmount: 150 }");
       });
     });
@@ -1075,7 +1075,7 @@ describe('e2e', function () {
       createReadStream(
         path.resolve(__dirname, 'fixtures', 'asi-script.js')
       ).pipe(shell.process.stdin);
-      await eventually(() => {
+      await shell.eventually(() => {
         shell.assertContainsOutput('admin;system.version;');
       });
     });
@@ -1154,7 +1154,7 @@ describe('e2e', function () {
               'load'
             ),
           });
-          await eventually(() => {
+          await shell.eventually(() => {
             shell.assertContainsOutput('hello one');
           });
           // We can't assert the exit code here currently because that breaks
@@ -1198,7 +1198,7 @@ describe('e2e', function () {
                 'load'
               ),
             });
-            await eventually(() => {
+            await shell.eventually(() => {
               shell.assertContainsOutput('Error: uh oh');
             });
             expect(await shell.waitForExit()).to.equal(1);
@@ -1212,7 +1212,7 @@ describe('e2e', function () {
           const shell = this.startTestShell({
             args: ['--nodb', ...jsContextFlags, '--eval', script],
           });
-          await eventually(() => {
+          await shell.eventually(() => {
             shell.assertContainsOutput('hello one');
           });
           expect(await shell.waitForExit()).to.equal(0);
@@ -1240,7 +1240,7 @@ describe('e2e', function () {
               'throw new Error("uh oh")',
             ],
           });
-          await eventually(() => {
+          await shell.eventually(() => {
             shell.assertContainsOutput('Error: uh oh');
           });
           expect(await shell.waitForExit()).to.equal(1);
@@ -1255,7 +1255,7 @@ describe('e2e', function () {
               'setImmediate(() => { throw new Error("uh oh"); })',
             ],
           });
-          await eventually(() => {
+          await shell.eventually(() => {
             shell.assertContainsOutput('Error: uh oh');
           });
           expect(await shell.waitForExit()).to.equal(
@@ -1272,7 +1272,7 @@ describe('e2e', function () {
               'void Promise.resolve().then(() => { throw new Error("uh oh"); })',
             ],
           });
-          await eventually(() => {
+          await shell.eventually(() => {
             shell.assertContainsOutput('Error: uh oh');
           });
           expect(await shell.waitForExit()).to.equal(
@@ -1478,7 +1478,7 @@ describe('e2e', function () {
       describe('log file', function () {
         it('creates a log file that keeps track of session events', async function () {
           expect(await shell.executeLine('print(123 + 456)')).to.include('579');
-          await eventually(async () => {
+          await shell.eventually(async () => {
             const log = await readLogfile();
             expect(
               log.filter((logEntry) => /Evaluating input/.test(logEntry.msg))
@@ -1514,7 +1514,7 @@ describe('e2e', function () {
           shell = await startTestShell();
           // Arrow up twice to skip the .exit line
           shell.writeInput('\u001b[A\u001b[A');
-          await eventually(() => {
+          await shell.eventually(() => {
             expect(shell.output).to.include('a = 42');
           });
           shell.writeInput('\n.exit\n');
@@ -1639,7 +1639,7 @@ describe('e2e', function () {
       it('keeps working when the home directory cannot be created at all', async function () {
         await fs.writeFile(homedir, 'this is a file and not a directory');
         const shell = await startTestShell();
-        await eventually(() => {
+        await shell.eventually(() => {
           expect(shell.output).to.include('Warning: Could not access file:');
         });
         expect(await shell.executeLine('print(123 + 456)')).to.include('579');
@@ -1653,7 +1653,7 @@ describe('e2e', function () {
         await fs.mkdir(path.dirname(logBasePath), { recursive: true });
         await fs.writeFile(logBasePath, 'also not a directory');
         const shell = await startTestShell();
-        await eventually(() => {
+        await shell.eventually(() => {
           expect(shell.output).to.include('Warning: Could not access file:');
         });
         expect(await shell.executeLine('print(123 + 456)')).to.include('579');
@@ -1678,7 +1678,7 @@ describe('e2e', function () {
         await fs.writeFile(configPath, '{}');
         await fs.chmod(configPath, 0); // Remove all permissions
         const shell = await startTestShell();
-        await eventually(() => {
+        await shell.eventually(() => {
           expect(shell.output).to.include('Warning: Could not access file:');
         });
         expect(await shell.executeLine('print(123 + 456)')).to.include('579');
diff --git a/packages/e2e-tests/test/test-shell.ts b/packages/e2e-tests/test/test-shell.ts
index 66565a1a1..21ad1dce8 100644
--- a/packages/e2e-tests/test/test-shell.ts
+++ b/packages/e2e-tests/test/test-shell.ts
@@ -9,7 +9,6 @@ import { inspect } from 'util';
 import path from 'path';
 import stripAnsi from 'strip-ansi';
 import { EJSON } from 'bson';
-import { eventually } from '../../../testing/eventually';
 
 /* eslint-disable mocha/no-exports -- This file export hooks wrapping Mocha's Hooks APIs */
 
@@ -144,6 +143,7 @@ export class TestShell {
   private _output: string;
   private _rawOutput: string;
   private _onClose: Promise<number>;
+  private _previousOutputLength = 0;
 
   constructor(
     shellProcess: ChildProcessWithoutNullStreams,
@@ -165,10 +165,7 @@ export class TestShell {
       });
     }
 
-    this._onClose = (async () => {
-      const [code] = await once(shellProcess, 'close');
-      return code;
-    })();
+    this._onClose = once(shellProcess, 'close').then(([code]) => code);
   }
 
   get output(): string {
@@ -183,39 +180,19 @@ export class TestShell {
     return this._process;
   }
 
-  async waitForPrompt(start = 0): Promise<void> {
-    await eventually(() => {
-      const output = this._output.slice(start);
+  /**
+   * Wait for the last line of the output to become a prompt and resolve with it
+   */
+  async waitForPrompt(start = 0): Promise<string> {
+    return this.eventually(() => {
+      const output = this._output.slice(start).trim();
       const lines = output.split('\n');
-      const found = !!lines
-        .filter((l) => PROMPT_PATTERN.exec(l)) // a line that is the prompt must at least match the pattern
-        .find((l) => {
-          // in some situations the prompt occurs multiple times in the line (but only in tests!)
-          const prompts = l
-            .trim()
-            .replace(/>$/g, '')
-            .split('>')
-            .map((m) => m.trim());
-          // if there are multiple prompt parts they must all equal
-          if (prompts.length > 1) {
-            for (const p of prompts) {
-              if (p !== prompts[0]) {
-                return false;
-              }
-            }
-          }
-          return true;
-        });
-      if (!found) {
-        throw new assert.AssertionError({
-          message: 'expected prompt',
-          expected: PROMPT_PATTERN.toString(),
-          actual:
-            this._output.slice(0, start) +
-            '[prompt search starts here]' +
-            output,
-        });
-      }
+      const lastLine = lines[lines.length - 1];
+      assert(
+        PROMPT_PATTERN.test(lastLine),
+        `Expected a prompt (last line was "${lastLine}")`
+      );
+      return lastLine;
     });
   }
 
@@ -239,6 +216,64 @@ export class TestShell {
     ]);
   }
 
+  /**
+   * Like the `eventually` utility, but instead of calling the callback on a timer,
+   * the callback is called as output is emitted.
+   */
+  eventually<T = unknown>(
+    cb: () => Promise<T> | T,
+    { timeout = 10_000 }: { timeout?: number } = {}
+  ) {
+    return new Promise<T>((resolve, reject) => {
+      const { stdout, stderr } = this._process;
+      let lastError: Error | null = null;
+      let currentCheck = Promise.resolve();
+
+      const timeoutTimer = setTimeout(() => {
+        cleanUp();
+        reject(
+          new Error(
+            `Timed out (waited ${timeout}ms): ${
+              lastError instanceof Error ? lastError.message : 'No cause'
+            }`
+          )
+        );
+      }, timeout);
+
+      function check() {
+        // Awaits any previous check to ensure there's only one check in-flight
+        // This is to prevent a new call to the `cb` if a previous call returned a promise which hasn't yet resolved
+        currentCheck = currentCheck.then(async () => {
+          try {
+            const result = await cb();
+            cleanUp();
+            resolve(result);
+          } catch (err) {
+            if (err instanceof Error) {
+              lastError = err;
+            } else {
+              throw new Error(
+                'Expected the callback to throw instances of Error'
+              );
+            }
+          }
+        }, reject);
+      }
+
+      function cleanUp() {
+        stdout.off('data', check);
+        stderr.off('data', check);
+        clearTimeout(timeoutTimer);
+      }
+
+      // Check as the process emits output
+      stdout.on('data', check);
+      stderr.on('data', check);
+      // Check right away
+      process.nextTick(check);
+    });
+  }
+
   kill(signal?: SignalType): void {
     this._process.kill(signal);
   }
@@ -249,14 +284,25 @@ export class TestShell {
   }
 
   writeInputLine(chars: string): void {
-    this.writeInput(`${chars}\n`);
+    this.writeInput(`${chars.trim()}\n`);
   }
 
   async executeLine(line: string): Promise<string> {
-    const previousOutputLength = this._output.length;
+    // Waiting for a prompt to appear since the last execution
+    await this.waitForPrompt(this._previousOutputLength);
+    // Keeping an the length of the output to return only output as result of the input
+    const outputLengthBefore = this._output.length;
     this.writeInputLine(line);
-    await this.waitForPrompt(previousOutputLength);
-    return this._output.slice(previousOutputLength);
+    // Wait for the execution and a new prompt to appear
+    const prompt = await this.waitForPrompt(outputLengthBefore);
+    // Store the output (excluding the following prompt)
+    const output = this._output.slice(
+      outputLengthBefore,
+      this._output.length - prompt.length - 1
+    );
+    // Storing the output for future executions
+    this._previousOutputLength = outputLengthBefore + output.length;
+    return output;
   }
 
   async executeLineWithJSONResult(line: string): Promise<any> {