diff --git a/lib/src/command/upgrade.dart b/lib/src/command/upgrade.dart
index 7078ac01014..8f12391ac35 100644
--- a/lib/src/command/upgrade.dart
+++ b/lib/src/command/upgrade.dart
@@ -17,6 +17,7 @@ import '../package_name.dart';
 import '../pubspec.dart';
 import '../pubspec_utils.dart';
 import '../solver.dart';
+import '../solver/version_solver.dart';
 import '../utils.dart';
 
 /// Handles the `upgrade` pub command.
@@ -25,9 +26,16 @@ class UpgradeCommand extends PubCommand {
   String get name => 'upgrade';
   @override
   String get description =>
-      "Upgrade the current package's dependencies to latest versions.";
+      "Upgrade the current package's dependencies to latest versions.\n"
+      '\n'
+      'Append `:latest` to a dependency to require the latest available '
+      'version.\n'
+      '\n'
+      'Append `:resolvable` to require the newest version resolvable with the '
+      'rest of\n'
+      'the dependency graph.';
   @override
-  String get argumentsDescription => '[dependencies...]';
+  String get argumentsDescription => '[dependencies[:latest|:resolvable]...]';
   @override
   String get docUrl => 'https://dart.dev/tools/pub/cmd/pub-upgrade';
 
@@ -111,6 +119,15 @@ class UpgradeCommand extends PubCommand {
   late final Future<List<String>> _packagesToUpgrade =
       _computePackagesToUpgrade();
 
+  late final List<_UpgradeTarget> _upgradeTargets =
+      argResults.rest.map(_parseUpgradeTarget).toList();
+
+  late final Future<List<ConstraintAndCause>?> _additionalConstraints =
+      _upgradeTargetConstraints();
+
+  late final Future<Map<String, PackageId>> _latestResolvablePackages =
+      _computeLatestResolvablePackages();
+
   /// List of package names to upgrade, if empty then upgrade all packages.
   ///
   /// This allows the user to specify list of names that they want the
@@ -118,11 +135,11 @@ class UpgradeCommand extends PubCommand {
   Future<List<String>> _computePackagesToUpgrade() async {
     if (argResults.flag('unlock-transitive')) {
       final graph = await entrypoint.packageGraph;
-      return argResults.rest
+      return _upgradeTargets
           .expand(
-            (package) => graph
+            (target) => graph
                 .transitiveDependencies(
-                  package,
+                  target.name,
                   followDevDependenciesFromPackage: true,
                 )
                 .map((p) => p.name),
@@ -130,7 +147,7 @@ class UpgradeCommand extends PubCommand {
           .toSet()
           .toList();
     } else {
-      return argResults.rest;
+      return _upgradeTargets.map((target) => target.name).toList();
     }
   }
 
@@ -152,6 +169,18 @@ Consider using the Dart 2.19 sdk to migrate to null safety.''');
         ),
       );
     }
+    if (_upgradeTargets.any((target) => target.kind != null)) {
+      if (_upgradeMajorVersions) {
+        usageException(
+          'Cannot use `:latest` or `:resolvable` with `--major-versions`.',
+        );
+      }
+      if (_tighten) {
+        usageException(
+          'Cannot use `:latest` or `:resolvable` with `--tighten`.',
+        );
+      }
+    }
 
     if (_upgradeMajorVersions) {
       if (argResults.flag('example')) {
@@ -196,6 +225,7 @@ Consider using the Dart 2.19 sdk to migrate to null safety.''');
     await e.acquireDependencies(
       SolveType.upgrade,
       unlock: await _packagesToUpgrade,
+      additionalConstraints: await _additionalConstraints,
       dryRun: _dryRun,
       precompile: _precompile,
       summaryOnly: onlySummary,
@@ -204,6 +234,118 @@ Consider using the Dart 2.19 sdk to migrate to null safety.''');
     _showOfflineWarning();
   }
 
+  Future<List<ConstraintAndCause>?> _upgradeTargetConstraints() async {
+    final constraintFutures = <Future<ConstraintAndCause>>[];
+    for (final target in _upgradeTargets) {
+      final kind = target.kind;
+      if (kind == null) continue;
+
+      constraintFutures.add(
+        (() async {
+          final targetPackage = switch (kind) {
+            _UpgradeTargetKind.latest => await _latest(target.name),
+            _UpgradeTargetKind.resolvable => await _latestResolvable(
+              target.name,
+            ),
+          };
+          return ConstraintAndCause(
+            targetPackage.toRange(),
+            '${targetPackage.name} ${targetPackage.version} was requested by '
+            '`$topLevelProgram pub upgrade ${target.argument}`.',
+          );
+        })(),
+      );
+    }
+    final constraints = await Future.wait(constraintFutures);
+    return constraints.isEmpty ? null : constraints;
+  }
+
+  Future<Map<String, PackageId>> _computeLatestResolvablePackages() async {
+    final solveResult = await log.spinner('Resolving dependencies', () async {
+      return await resolveVersions(
+        SolveType.upgrade,
+        cache,
+        entrypoint.workspaceRoot.transformWorkspace(
+          (package) => stripVersionBounds(package.pubspec),
+        ),
+      );
+    }, condition: _shouldShowSpinner);
+    return {for (final package in solveResult.packages) package.name: package};
+  }
+
+  Future<PackageId> _latestResolvable(String package) async {
+    if (_packageRef(package) == null) {
+      dataError('Package `$package` is not in the current resolution.');
+    }
+    final latestResolvable = (await _latestResolvablePackages)[package];
+    if (latestResolvable == null) {
+      dataError(
+        'Package `$package` is not in the latest resolvable resolution.',
+      );
+    }
+    return latestResolvable;
+  }
+
+  Future<PackageId> _latest(String package) async {
+    final ref = _packageRef(package);
+    if (ref == null) {
+      dataError('Package `$package` is not in the current resolution.');
+    }
+    final current = entrypoint.lockFile.packages[package];
+    final latest = await cache.getLatest(ref, version: current?.version);
+    if (latest == null) {
+      dataError('Could not find package `$package`.');
+    }
+    return latest;
+  }
+
+  PackageRef? _packageRef(String package) {
+    final current = entrypoint.lockFile.packages[package];
+    if (current != null) return current.toRef();
+
+    for (final workspacePackage
+        in entrypoint.workspaceRoot.transitiveWorkspace) {
+      final dependency = workspacePackage.dependencies[package];
+      if (dependency != null) return dependency.toRef();
+      final devDependency = workspacePackage.devDependencies[package];
+      if (devDependency != null) return devDependency.toRef();
+    }
+    return null;
+  }
+
+  _UpgradeTarget _parseUpgradeTarget(String argument) {
+    final parts = argument.split(':');
+    if (parts.length > 2) {
+      usageException(
+        'Could not parse upgrade target `$argument`. Use `<package>`, '
+        '`<package>:latest`, or `<package>:resolvable`.',
+      );
+    }
+
+    final package = parts.first;
+    if (!packageNameRegExp.hasMatch(package)) {
+      usageException('Not a valid package name: "$package"');
+    }
+
+    if (parts.length == 1) {
+      return _UpgradeTarget(argument, package, null);
+    }
+
+    final suffix = parts.last;
+    final kind = switch (suffix) {
+      'latest' => _UpgradeTargetKind.latest,
+      'resolvable' => _UpgradeTargetKind.resolvable,
+      _ => null,
+    };
+    if (kind == null) {
+      usageException(
+        'Unknown upgrade target `$argument`. Use `<package>`, '
+        '`<package>:latest`, or `<package>:resolvable`.',
+      );
+    }
+    return _UpgradeTarget(argument, package, kind);
+  }
+
   /// Return names of packages to be upgraded, and throws [UsageException] if
   /// any package names not in the direct dependencies or dev_dependencies are
   /// given.
@@ -240,21 +382,7 @@ be direct 'dependencies' or 'dev_dependencies', following packages are not:
 
   Future<void> _runUpgradeMajorVersions() async {
     final toUpgrade = await _directDependenciesToUpgrade();
-    // Solve [resolvablePubspec] in-memory and consolidate the resolved
-    // versions of the packages into a map for quick searching.
-    final resolvedPackages = <String, PackageId>{};
-    final solveResult = await log.spinner('Resolving dependencies', () async {
-      return await resolveVersions(
-        SolveType.upgrade,
-        cache,
-        entrypoint.workspaceRoot.transformWorkspace(
-          (package) => stripVersionBounds(package.pubspec),
-        ),
-      );
-    }, condition: _shouldShowSpinner);
-    for (final resolvedPackage in solveResult.packages) {
-      resolvedPackages[resolvedPackage.name] = resolvedPackage;
-    }
+    final resolvedPackages = await _latestResolvablePackages;
     final dependencyOverriddenDeps = <String>[];
     // Changes to be made to `pubspec.yaml` of each package.
     // Mapping from original to changed value.
@@ -377,3 +505,13 @@ be direct 'dependencies' or 'dev_dependencies', following packages are not:
     }
   }
 }
+
+enum _UpgradeTargetKind { latest, resolvable }
+
+class _UpgradeTarget {
+  final String argument;
+  final String name;
+  final _UpgradeTargetKind? kind;
+
+  _UpgradeTarget(this.argument, this.name, this.kind);
+}
diff --git a/lib/src/entrypoint.dart b/lib/src/entrypoint.dart
index 314729a4453..68ee0e06735 100644
--- a/lib/src/entrypoint.dart
+++ b/lib/src/entrypoint.dart
@@ -35,6 +35,7 @@ import 'sdk/flutter.dart';
 import 'solver.dart';
 import 'solver/report.dart';
 import 'solver/solve_suggestions.dart';
+import 'solver/version_solver.dart';
 import 'source/cached.dart';
 import 'source/hosted.dart';
 import 'source/root.dart';
@@ -556,6 +557,10 @@ See $workspacesDocUrl for more information.''',
   /// The iterable [unlock] specifies the list of packages whose versions can be
   /// changed even if they are locked in the pubspec.lock file.
   ///
+  /// The iterable [additionalConstraints] specifies extra constraints the
+  /// version solver must satisfy. When omitted, no extra constraints are
+  /// applied.
+  ///
   /// Shows a report of the changes made relative to the previous lockfile. If
   /// this is an upgrade or downgrade, all transitive dependencies are shown in
   /// the report. Otherwise, only dependencies that were changed are shown. If
@@ -575,6 +580,7 @@ See $workspacesDocUrl for more information.''',
   Future<void> acquireDependencies(
     SolveType type, {
     Iterable<String> unlock = const [],
+    Iterable<ConstraintAndCause>? additionalConstraints,
     bool dryRun = false,
     bool precompile = false,
     bool summaryOnly = false,
@@ -608,6 +614,7 @@ Try running `$topLevelProgram pub get` to create `$lockFilePath`.''');
           workspaceRoot,
           lockFile: lockFile,
           unlock: unlock,
+          additionalConstraints: additionalConstraints,
         );
       });
     } on SolveFailure catch (e) {
diff --git a/test/testdata/goldens/help_test/pub upgrade --help.txt b/test/testdata/goldens/help_test/pub upgrade --help.txt
index 90030c7ca69..262edf55989 100644
--- a/test/testdata/goldens/help_test/pub upgrade --help.txt	
+++ b/test/testdata/goldens/help_test/pub upgrade --help.txt	
@@ -4,7 +4,12 @@
 $ pub upgrade --help
 Upgrade the current package's dependencies to latest versions.
 
-Usage: pub upgrade [dependencies...]
+Append `:latest` to a dependency to require the latest available version.
+
+Append `:resolvable` to require the newest version resolvable with the rest of
+the dependency graph.
+
+Usage: pub upgrade [dependencies[:latest|:resolvable]...]
 -h, --help                 Print this usage information.
     --[no-]offline         Use cached packages instead of accessing the network.
 -n, --dry-run              Report what dependencies would change but don't change any.
diff --git a/test/upgrade/upgrade_transitive_test.dart b/test/upgrade/upgrade_transitive_test.dart
index 05fea6d994a..5e92e6f25d6 100644
--- a/test/upgrade/upgrade_transitive_test.dart
+++ b/test/upgrade/upgrade_transitive_test.dart
@@ -5,6 +5,7 @@
 @TestOn('vm')
 library;
 
+import 'package:pub/src/exit_codes.dart' as exit_codes;
 import 'package:test/test.dart';
 
 import '../descriptor.dart' as d;
@@ -104,4 +105,162 @@ void main() {
       ),
     );
   });
+
+  test('`dependency:latest` explains why latest cannot be selected', () async {
+    final server = await servePackages();
+    server.serve('foo', '1.0.0', deps: {'bar': '^1.0.0'});
+    server.serve('bar', '1.0.0');
+
+    await d.appDir(dependencies: {'foo': '^1.0.0'}).create();
+
+    await pubGet(output: contains('+ foo 1.0.0'));
+
+    server.serve('bar', '2.0.0');
+
+    await pubUpgrade(
+      args: ['bar:latest'],
+      error: allOf(
+        contains('bar 2.0.0'),
+        contains('bar:latest'),
+        contains('foo'),
+        contains('bar ^1.0.0'),
+        contains('version solving failed'),
+      ),
+    );
+  });
+
+  test(
+    '`dependency:latest` upgrades a transitive dependency to latest',
+    () async {
+      final server = await servePackages();
+      server.serve('foo', '1.0.0', deps: {'bar': 'any'});
+      server.serve('bar', '1.0.0');
+
+      await d.appDir(dependencies: {'foo': '^1.0.0'}).create();
+
+      await pubGet(output: contains('+ foo 1.0.0'));
+
+      server.serve('bar', '2.0.0');
+
+      await pubUpgrade(args: ['bar:latest'], output: contains('> bar 2.0.0'));
+    },
+  );
+
+  test('`dependency:resolvable` upgrades a transitive dependency to latest '
+      'resolvable', () async {
+    final server = await servePackages();
+    server.serve('foo', '1.0.0', deps: {'bar': '^1.0.0'});
+    server.serve('bar', '1.0.0');
+
+    await d.appDir(dependencies: {'foo': '^1.0.0'}).create();
+
+    await pubGet(output: contains('+ foo 1.0.0'));
+
+    server.serve('bar', '1.5.0');
+    server.serve('bar', '2.0.0');
+
+    await pubUpgrade(
+      args: ['bar:resolvable'],
+      output: allOf(contains('> bar 1.5.0'), isNot(contains('bar 2.0.0'))),
+    );
+  });
+
+  test(
+    '`dependency:resolvable` explains why resolvable cannot be selected',
+    () async {
+      final server = await servePackages();
+      server.serve('foo', '1.0.0', deps: {'bar': '^1.0.0'});
+      server.serve('foo', '2.0.0', deps: {'bar': '^2.0.0'});
+      server.serve('bar', '1.0.0');
+
+      await d.appDir(dependencies: {'foo': '^1.0.0'}).create();
+
+      await pubGet(output: contains('+ foo 1.0.0'));
+
+      server.serve('bar', '2.0.0');
+
+      await pubUpgrade(
+        args: ['bar:resolvable'],
+        error: allOf(
+          contains('bar 2.0.0'),
+          contains('bar:resolvable'),
+          contains('foo'),
+          contains('bar ^1.0.0'),
+          contains('version solving failed'),
+        ),
+      );
+    },
+  );
+
+  test('multiple dependency targets resolve together', () async {
+    final server = await servePackages();
+    server.serve('foo', '1.0.0', deps: {'bar': 'any', 'baz': '^1.0.0'});
+    server.serve('bar', '1.0.0');
+    server.serve('baz', '1.0.0');
+
+    await d.appDir(dependencies: {'foo': '^1.0.0'}).create();
+
+    await pubGet(output: contains('+ foo 1.0.0'));
+
+    server.serve('foo', '1.5.0', deps: {'bar': 'any', 'baz': '^1.0.0'});
+    server.serve('bar', '2.0.0');
+    server.serve('baz', '1.5.0');
+    server.serve('baz', '2.0.0');
+
+    await pubUpgrade(
+      args: ['foo', 'bar:latest', 'baz:resolvable'],
+      output: allOf(
+        contains('> foo 1.5.0'),
+        contains('> bar 2.0.0'),
+        contains('> baz 1.5.0'),
+        isNot(contains('baz 2.0.0')),
+      ),
+    );
+  });
+
+  test(
+    '`dependency:latest` requires a package from the current resolution',
+    () async {
+      await servePackages();
+      await d.appDir(dependencies: {'foo': '^1.0.0'}).create();
+
+      await pubUpgrade(
+        args: ['missing:latest'],
+        error: contains('Package `missing` is not in the current resolution.'),
+        exitCode: exit_codes.DATA,
+      );
+    },
+  );
+
+  test(
+    '`dependency:latest` cannot be combined with --major-versions',
+    () async {
+      await servePackages();
+      await d.appDir(dependencies: {'foo': '^1.0.0'}).create();
+
+      await pubUpgrade(
+        args: ['--major-versions', 'foo:latest'],
+        error: contains(
+          'Cannot use `:latest` or `:resolvable` with `--major-versions`.',
+        ),
+        exitCode: exit_codes.USAGE,
+      );
+    },
+  );
+
+  test('dependency target cannot contain multiple colons', () async {
+    await servePackages();
+    await d.appDir(dependencies: {'foo': '^1.0.0'}).create();
+
+    await pubUpgrade(
+      args: ['foo:bar:latest'],
+      error: allOf(
+        contains('Could not parse upgrade target `foo:bar:latest`.'),
+        contains('Use `<package>`'),
+        contains('`<package>:latest`'),
+        contains('`<package>:resolvable`.'),
+      ),
+      exitCode: exit_codes.USAGE,
+    );
+  });
 }