diff --git a/CHANGELOG.md b/CHANGELOG.md
index 2b0803f38c..847d34437a 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -2,6 +2,9 @@
 
 ## Main branch (git)
 
+- Bug fix: Make sure command parser gives precedence to longer cmd-aliases. So
+  if sending `smile at` and the cmd `smile` has alias `smile at`, the match is
+  ordered so the result is never interpreted as `smile` with an argument `at`.
 - Bug fix: || (escaped color tags) were parsed too early in help entries,
   leading to colors when wanting a | separator
 - Bug fix: Make sure spawned objects get `typeclass_path` pointing to the true
diff --git a/evennia/commands/command.py b/evennia/commands/command.py
index 9dac840128..cca0e35754 100644
--- a/evennia/commands/command.py
+++ b/evennia/commands/command.py
@@ -11,7 +11,6 @@ import re
 from django.conf import settings
 from django.urls import reverse
 from django.utils.text import slugify
-
 from evennia.locks.lockhandler import LockHandler
 from evennia.utils.ansi import ANSIString
 from evennia.utils.evtable import EvTable
@@ -54,10 +53,14 @@ def _init_command(cls, **kwargs):
             cls.aliases = []
     cls.aliases = list(set(alias for alias in cls.aliases if alias and alias != cls.key))
 
-    # optimization - a set is much faster to match against than a list
+    # optimization - a set is much faster to match against than a list. This is useful
+    # for 'does any match' kind of queries
     cls._matchset = set([cls.key] + cls.aliases)
-    # optimization for looping over keys+aliases
-    cls._keyaliases = tuple(cls._matchset)
+    # optimization for looping over keys+aliases. We sort by longest entry first, since we
+    # want to be able to catch commands with spaces in the alias/key (so if you have key 'smile'
+    # and alias 'smile at', writing 'smile at' should not risk being interpreted as 'smile'
+    # with an argument 'at')
+    cls._keyaliases = tuple(sorted([cls.key] + cls.aliases, key=len, reverse=True))
 
     # by default we don't save the command between runs
     if not hasattr(cls, "save_for_next"):
@@ -303,10 +306,13 @@ class Command(metaclass=CommandMeta):
         matches.extend(x.lower() for x in self.aliases)
 
         self._matchset = set(matches)
-        # optimization for looping over keys+aliases
-        self._keyaliases = tuple(self._matchset)
+        # optimization for looping over keys+aliases. We sort by longest entry first, since we
+        # want to be able to catch commands with spaces in the alias/key (so if you have key 'smile'
+        # and alias 'smile at', writing 'smile at' should not risk being interpreted as 'smile'
+        # with an argument 'at')
+        self._keyaliases = tuple(sorted(matches, key=len, reverse=True))
 
-        self._noprefix_aliases = {x.lstrip(CMD_IGNORE_PREFIXES): x for x in matches}
+        self._noprefix_aliases = {x.lstrip(CMD_IGNORE_PREFIXES): x for x in self._keyaliases}
 
     def set_key(self, new_key):
         """
diff --git a/evennia/commands/tests.py b/evennia/commands/tests.py
index c2357c00c6..a70572e6fc 100644
--- a/evennia/commands/tests.py
+++ b/evennia/commands/tests.py
@@ -4,7 +4,6 @@ Unit testing for the Command system itself.
 """
 
 from django.test import override_settings
-
 from evennia.commands import cmdparser
 from evennia.commands.cmdset import CmdSet
 from evennia.commands.command import Command
@@ -991,9 +990,8 @@ class TestOptionTransferReplace(TestCase):
 
 import sys
 
-from twisted.trial.unittest import TestCase as TwistedTestCase
-
 from evennia.commands import cmdhandler
+from twisted.trial.unittest import TestCase as TwistedTestCase
 
 
 def _mockdelay(time, func, *args, **kwargs):
@@ -1232,3 +1230,35 @@ class TestCmdSet(BaseEvenniaTest):
         result = test_cmd_set.get("another command")
 
         self.assertIsInstance(result, _CmdTest2)
+
+
+class _CmdG(Command):
+    key = "smile"
+    aliases = ["smile at", "grin", "grin at"]
+
+
+class _CmdSetG(CmdSet):
+    def at_cmdset_creation(self):
+        self.add(_CmdG())
+
+
+class TestIssue3090(BaseEvenniaTest):
+    """
+    Command aliases should be prioritized longest-match to shortest-match.
+    https://github.com/evennia/evennia/issues/3090
+
+    """
+
+    def test_long_aliases(self):
+
+        cmdset_g = _CmdSetG()
+
+        # print(cmdset_g.commands[0]._keyaliases)
+
+        result = cmdparser.cmdparser("smile at", cmdset_g, None)[0]
+        self.assertEqual(result[0], "smile at")
+        self.assertEqual(result[1], "")
+        self.assertEqual(result[2].__class__, _CmdG)
+        self.assertEqual(result[3], 8)
+        self.assertEqual(result[4], 1.0)
+        self.assertEqual(result[5], "smile at")