diff --git a/packages/utils/upgrade/src/cli/commands/upgrade.ts b/packages/utils/upgrade/src/cli/commands/upgrade.ts
index cd419651fc..c54c4ae4fb 100644
--- a/packages/utils/upgrade/src/cli/commands/upgrade.ts
+++ b/packages/utils/upgrade/src/cli/commands/upgrade.ts
@@ -2,6 +2,7 @@ import prompts from 'prompts';
 import { InvalidArgumentError, Option } from 'commander';
 
 import type { Command } from 'commander';
+
 import { loggerFactory } from '../../modules/logger';
 import { Version, isLiteralSemVer, isValidSemVer, semVerFactory } from '../../modules/version';
 import { handleError } from '../errors';
@@ -71,6 +72,12 @@ export const register = (program: Command) => {
       });
   };
 
+  // upgrade latest
+  addReleaseUpgradeCommand(
+    Version.ReleaseType.Latest,
+    'Upgrade to the latest available version of Strapi'
+  );
+
   // upgrade major
   addReleaseUpgradeCommand(
     Version.ReleaseType.Major,
diff --git a/packages/utils/upgrade/src/cli/errors.ts b/packages/utils/upgrade/src/cli/errors.ts
index ab503cc892..4ca6d3fcd5 100644
--- a/packages/utils/upgrade/src/cli/errors.ts
+++ b/packages/utils/upgrade/src/cli/errors.ts
@@ -1,6 +1,13 @@
 import chalk from 'chalk';
 
+import { AbortedError } from '../modules/error';
+
 export const handleError = (err: unknown, isSilent: boolean) => {
+  // If the upgrade process has been aborted, exit silently
+  if (err instanceof AbortedError) {
+    process.exit(0);
+  }
+
   if (!isSilent) {
     console.error(
       chalk.red(`[ERROR]\t[${new Date().toISOString()}]`),
diff --git a/packages/utils/upgrade/src/modules/error/utils.ts b/packages/utils/upgrade/src/modules/error/utils.ts
index 014f8cb1c7..ae448a599c 100644
--- a/packages/utils/upgrade/src/modules/error/utils.ts
+++ b/packages/utils/upgrade/src/modules/error/utils.ts
@@ -19,6 +19,12 @@ export class NPMCandidateNotFoundError extends Error {
   }
 }
 
+export class AbortedError extends Error {
+  constructor(message: string = 'Upgrade aborted') {
+    super(message);
+  }
+}
+
 export const unknownToError = (e: unknown): Error => {
   if (e instanceof Error) {
     return e;
diff --git a/packages/utils/upgrade/src/modules/upgrader/types.ts b/packages/utils/upgrade/src/modules/upgrader/types.ts
index 3e4854964a..d5be46ec3c 100644
--- a/packages/utils/upgrade/src/modules/upgrader/types.ts
+++ b/packages/utils/upgrade/src/modules/upgrader/types.ts
@@ -1,9 +1,15 @@
+import type { NPM } from '../npm';
+import type { AppProject } from '../project';
 import type { Version } from '../version';
 import type { Requirement } from '../requirement';
 import type { Logger } from '../logger';
 import type { ConfirmationCallback } from '../common/types';
 
 export interface Upgrader {
+  getNPMPackage(): NPM.Package;
+  getProject(): AppProject;
+  getTarget(): Version.SemVer;
+
   setTarget(target: Version.SemVer): this;
   setRequirements(requirements: Requirement.Requirement[]): this;
   setLogger(logger: Logger): this;
@@ -14,6 +20,8 @@ export interface Upgrader {
   dry(enabled?: boolean): this;
   onConfirm(callback: ConfirmationCallback | null): this;
 
+  confirm(message: string): Promise<boolean>;
+
   addRequirement(requirement: Requirement.Requirement): this;
 
   upgrade(): Promise<UpgradeReport>;
diff --git a/packages/utils/upgrade/src/modules/upgrader/upgrader.ts b/packages/utils/upgrade/src/modules/upgrader/upgrader.ts
index 77195e1610..b644090025 100644
--- a/packages/utils/upgrade/src/modules/upgrader/upgrader.ts
+++ b/packages/utils/upgrade/src/modules/upgrader/upgrader.ts
@@ -57,6 +57,18 @@ export class Upgrader implements UpgraderInterface {
     this.confirmationCallback = null;
   }
 
+  getNPMPackage(): NPM.Package {
+    return this.npmPackage;
+  }
+
+  getProject(): AppProject {
+    return this.project;
+  }
+
+  getTarget(): Version.SemVer {
+    return semVerFactory(this.target.raw);
+  }
+
   setRequirements(requirements: Requirement.Requirement[]) {
     this.requirements = requirements;
     return this;
@@ -172,6 +184,14 @@ export class Upgrader implements UpgraderInterface {
     return successReport();
   }
 
+  async confirm(message: string): Promise<boolean> {
+    if (typeof this.confirmationCallback !== 'function') {
+      return true;
+    }
+
+    return this.confirmationCallback(message);
+  }
+
   private async checkRequirements(
     requirements: Requirement.Requirement[],
     context: Requirement.TestContext
@@ -292,10 +312,13 @@ export class Upgrader implements UpgraderInterface {
 
   private async runCodemods(range: Version.Range): Promise<void> {
     const codemodRunner = codemodRunnerFactory(this.project, range);
+
     codemodRunner.dry(this.isDry);
+
     if (this.logger) {
       codemodRunner.setLogger(this.logger);
     }
+
     await codemodRunner.run();
   }
 }
diff --git a/packages/utils/upgrade/src/modules/version/__tests__/range.test.ts b/packages/utils/upgrade/src/modules/version/__tests__/range.test.ts
index 0e0e601d6a..0acdedc0d9 100644
--- a/packages/utils/upgrade/src/modules/version/__tests__/range.test.ts
+++ b/packages/utils/upgrade/src/modules/version/__tests__/range.test.ts
@@ -22,6 +22,30 @@ describe('Version Utilities', () => {
       expect(range.raw).toBe('>1.0.0 <=2');
     });
 
+    it('should create a range for Minor release type', () => {
+      const currentVersion = new semver.SemVer('1.0.0');
+
+      const range = rangeFromReleaseType(currentVersion, Version.ReleaseType.Minor);
+      expect(range).toBeInstanceOf(semver.Range);
+      expect(range.raw).toBe('>1.0.0 <2.0.0');
+    });
+
+    it('should create a range for Patch release type', () => {
+      const currentVersion = new semver.SemVer('1.0.0');
+
+      const range = rangeFromReleaseType(currentVersion, Version.ReleaseType.Patch);
+      expect(range).toBeInstanceOf(semver.Range);
+      expect(range.raw).toBe('>1.0.0 <1.1.0');
+    });
+
+    it('should create a range for Latest release type', () => {
+      const currentVersion = new semver.SemVer('1.0.0');
+
+      const range = rangeFromReleaseType(currentVersion, Version.ReleaseType.Latest);
+      expect(range).toBeInstanceOf(semver.Range);
+      expect(range.raw).toBe('>1.0.0');
+    });
+
     it('should throw for unsupported release types', () => {
       const currentVersion = new semver.SemVer('1.0.0');
       expect(() =>
diff --git a/packages/utils/upgrade/src/modules/version/__tests__/semver.test.ts b/packages/utils/upgrade/src/modules/version/__tests__/semver.test.ts
index 9f43cdb97c..485e2694a1 100644
--- a/packages/utils/upgrade/src/modules/version/__tests__/semver.test.ts
+++ b/packages/utils/upgrade/src/modules/version/__tests__/semver.test.ts
@@ -43,6 +43,7 @@ describe('Version Utilities', () => {
       expect(isSemVerReleaseType(Version.ReleaseType.Major)).toBe(true);
       expect(isSemVerReleaseType(Version.ReleaseType.Minor)).toBe(true);
       expect(isSemVerReleaseType(Version.ReleaseType.Patch)).toBe(true);
+      expect(isSemVerReleaseType(Version.ReleaseType.Latest)).toBe(true);
     });
 
     it('should return false for invalid release types', () => {
diff --git a/packages/utils/upgrade/src/modules/version/range.ts b/packages/utils/upgrade/src/modules/version/range.ts
index 0fba26100e..889b8236a7 100644
--- a/packages/utils/upgrade/src/modules/version/range.ts
+++ b/packages/utils/upgrade/src/modules/version/range.ts
@@ -9,12 +9,16 @@ export const rangeFactory = (range: string): Version.Range => {
 
 export const rangeFromReleaseType = (current: Version.SemVer, identifier: Version.ReleaseType) => {
   switch (identifier) {
+    case Version.ReleaseType.Latest: {
+      // Match anything greater than the current version
+      return rangeFactory(`>${current.raw}`);
+    }
     case Version.ReleaseType.Major: {
       // For example, 4.15.4 returns 5.0.0
       const nextMajor = semVerFactory(current.raw).inc('major');
 
-      // Using only the major version as upper limit allows any minor,
-      // patch or build version to be taken in the range.
+      // Using only the major version as the upper limit allows any minor,
+      // patch, or build version to be taken in the range.
       //
       // For example, if the current version is "4.15.4", incrementing the
       // major version would result in "5.0.0".
diff --git a/packages/utils/upgrade/src/modules/version/types.ts b/packages/utils/upgrade/src/modules/version/types.ts
index 82fb9e48f8..d1c27b9d99 100644
--- a/packages/utils/upgrade/src/modules/version/types.ts
+++ b/packages/utils/upgrade/src/modules/version/types.ts
@@ -10,7 +10,10 @@ export type LiteralSemVer = `${Version}.${Version}.${Version}`;
 export type { SemVer, Range } from 'semver';
 
 export enum ReleaseType {
+  // Classic
   Major = 'major',
   Minor = 'minor',
   Patch = 'patch',
+  // Other
+  Latest = 'latest',
 }
diff --git a/packages/utils/upgrade/src/tasks/__tests__/codemods.test.ts b/packages/utils/upgrade/src/tasks/__tests__/codemods.test.ts
index 134e67fff5..80ccac66b3 100644
--- a/packages/utils/upgrade/src/tasks/__tests__/codemods.test.ts
+++ b/packages/utils/upgrade/src/tasks/__tests__/codemods.test.ts
@@ -30,7 +30,7 @@ describe('codemods task', () => {
     target: Version.ReleaseType.Major,
     logger,
     dry: false,
-    selectCodemods: (options) => Promise.resolve(options),
+    selectCodemods: <T>(options: T) => Promise.resolve(options),
   };
 
   (codemodRunnerFactory as jest.Mock).mockReturnValue({
diff --git a/packages/utils/upgrade/src/tasks/codemods/utils.ts b/packages/utils/upgrade/src/tasks/codemods/utils.ts
index ea803cd54b..319d12f084 100644
--- a/packages/utils/upgrade/src/tasks/codemods/utils.ts
+++ b/packages/utils/upgrade/src/tasks/codemods/utils.ts
@@ -18,6 +18,8 @@ export const getRangeFromTarget = (
   const { major, minor, patch } = currentVersion;
 
   switch (target) {
+    case Version.ReleaseType.Latest:
+      throw new Error("Can't use <latest> to create a codemods range: not implemented");
     case Version.ReleaseType.Major:
       return rangeFactory(`${major}`);
     case Version.ReleaseType.Minor:
diff --git a/packages/utils/upgrade/src/tasks/upgrade/prompts/index.ts b/packages/utils/upgrade/src/tasks/upgrade/prompts/index.ts
new file mode 100644
index 0000000000..d6c0d24fc6
--- /dev/null
+++ b/packages/utils/upgrade/src/tasks/upgrade/prompts/index.ts
@@ -0,0 +1 @@
+export * from './latest';
diff --git a/packages/utils/upgrade/src/tasks/upgrade/prompts/latest.ts b/packages/utils/upgrade/src/tasks/upgrade/prompts/latest.ts
new file mode 100644
index 0000000000..2b20e2d6a3
--- /dev/null
+++ b/packages/utils/upgrade/src/tasks/upgrade/prompts/latest.ts
@@ -0,0 +1,62 @@
+import { AbortedError } from '../../../modules/error';
+import * as f from '../../../modules/format';
+
+import { rangeFactory, semVerFactory, Version } from '../../../modules/version';
+
+import type { Upgrader } from '../../../modules/upgrader';
+import type { UpgradeOptions } from '../types';
+
+/**
+ * Handles the upgrade prompts when using the latest tag.
+ *
+ * - checks if an upgrade involves a major bump, warning and asking for user confirmation before proceeding
+ */
+export const latest = async (upgrader: Upgrader, options: UpgradeOptions) => {
+  // Exit if the upgrade target isn't the latest tag
+  if (options.target !== Version.ReleaseType.Latest) {
+    return;
+  }
+
+  // Retrieve utilities from the upgrader instance
+  const npmPackage = upgrader.getNPMPackage();
+  const target = upgrader.getTarget();
+  const project = upgrader.getProject();
+
+  const { strapiVersion: current } = project;
+
+  // Pre-formatted strings used in logs
+  const fTargetMajor = f.highlight(`v${target.major}`);
+  const fCurrentMajor = f.highlight(`v${current.major}`);
+
+  const fTarget = f.version(target);
+  const fCurrent = f.version(current);
+
+  // Flags
+  const isMajorUpgrade = target.major > current.major;
+
+  // Handle potential major upgrade, warns, and asks for confirmation to proceed
+  if (isMajorUpgrade) {
+    options.logger.warn(
+      `Detected a major upgrade for the "${f.highlight(Version.ReleaseType.Latest)}" tag: ${fCurrent} > ${fTarget}`
+    );
+
+    // Find the latest release in between the current one and the next major
+    const newerPackageRelease = npmPackage
+      .findVersionsInRange(rangeFactory(`>${current.raw} <${target.major}`))
+      .at(-1);
+
+    // If the project isn't on the latest version for the current major, emit a warning
+    if (newerPackageRelease) {
+      const fLatest = f.version(semVerFactory(newerPackageRelease.version));
+      options.logger.warn(
+        `It's recommended to first upgrade to the latest version of ${fCurrentMajor} (${fLatest}) before upgrading to ${fTargetMajor}.`
+      );
+    }
+
+    const proceedAnyway = await upgrader.confirm(`I know what I'm doing. Proceed anyway!`);
+
+    if (!proceedAnyway) {
+      throw new AbortedError();
+    }
+  }
+};
diff --git a/packages/utils/upgrade/src/tasks/upgrade/upgrade.ts b/packages/utils/upgrade/src/tasks/upgrade/upgrade.ts
index 0afd76a927..c6366e36e4 100644
--- a/packages/utils/upgrade/src/tasks/upgrade/upgrade.ts
+++ b/packages/utils/upgrade/src/tasks/upgrade/upgrade.ts
@@ -8,14 +8,16 @@ import { constants as upgraderConstants, upgraderFactory } from '../../modules/u
 import { Version } from '../../modules/version';
 
 import * as requirements from './requirements';
+import * as prompts from './prompts';
 
 import type { UpgradeOptions } from './types';
+import type { Upgrader } from '../../modules/upgrader';
 
 export const upgrade = async (options: UpgradeOptions) => {
   const timer = timerFactory();
   const { logger, codemodsTarget } = options;
 
-  // Make sure we're resolving the correct working directory based on the given input
+  // Resolves the correct working directory based on the given input
   const cwd = path.resolve(options.cwd ?? process.cwd());
 
   const project = projectFactory(cwd);
@@ -49,17 +51,11 @@ export const upgrade = async (options: UpgradeOptions) => {
     upgrader.overrideCodemodsTarget(codemodsTarget);
   }
 
-  // Don't add the same requirements when manually targeting a major upgrade
-  // using a semver as it's implied that the users know what they're doing
-  if (options.target === Version.ReleaseType.Major) {
-    upgrader
-      .addRequirement(requirements.major.REQUIRE_AVAILABLE_NEXT_MAJOR)
-      .addRequirement(requirements.major.REQUIRE_LATEST_FOR_CURRENT_MAJOR);
-  }
+  // Prompt user for confirmation details before upgrading
+  await runUpgradePrompts(upgrader, options);
 
-  // Make sure the git repository is in an optimal state before running the upgrade
-  // Mainly used to ease rollbacks in case the upgrade is corrupted
-  upgrader.addRequirement(requirements.common.REQUIRE_GIT.asOptional());
+  // Add specific requirements before upgrading
+  addUpgradeRequirements(upgrader, options);
 
   // Actually run the upgrade process once configured,
   // The response contains information about the final status: success/error
@@ -73,3 +69,23 @@ export const upgrade = async (options: UpgradeOptions) => {
 
   logger.info(`Completed in ${f.durationMs(timer.elapsedMs)}ms`);
 };
+
+const runUpgradePrompts = async (upgrader: Upgrader, options: UpgradeOptions) => {
+  if (options.target === Version.ReleaseType.Latest) {
+    await prompts.latest(upgrader, options);
+  }
+};
+
+const addUpgradeRequirements = (upgrader: Upgrader, options: UpgradeOptions): void => {
+  // Don't add the same requirements when manually targeting a major upgrade
+  // using a semver as it's implied that the users know what they're doing
+  if (options.target === Version.ReleaseType.Major) {
+    upgrader
+      .addRequirement(requirements.major.REQUIRE_AVAILABLE_NEXT_MAJOR)
+      .addRequirement(requirements.major.REQUIRE_LATEST_FOR_CURRENT_MAJOR);
+  }
+
+  // Make sure the git repository is in an optimal state before running the upgrade
+  // Mainly used to ease rollbacks in case the upgrade is corrupted
+  upgrader.addRequirement(requirements.common.REQUIRE_GIT.asOptional());
+};