diff --git a/CHANGELOG.md b/CHANGELOG.md
index 90df75b6..8869f094 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -7,6 +7,7 @@
 - Remove agent singleton so that client TLS certificates are reloaded on every API request.
 - Use Axios client to receive event stream so TLS settings are properly applied.
 - Set `usage-app=vscode` on `coder ssh` to fix deployment session counting.
+- Fix version comparison logic for checking wildcard support in "coder ssh"
 
 ## [v1.4.1](https://github.com/coder/vscode-coder/releases/tag/v1.4.1) (2025-02-19)
 
diff --git a/src/featureSet.test.ts b/src/featureSet.test.ts
index 4fa594ce..feff09d6 100644
--- a/src/featureSet.test.ts
+++ b/src/featureSet.test.ts
@@ -11,4 +11,12 @@ describe("check version support", () => {
       expect(featureSetForVersion(semver.parse(v)).proxyLogDirectory).toBeTruthy()
     })
   })
+  it("wildcard ssh", () => {
+    ;["v1.3.3+e491217", "v2.3.3+e491217"].forEach((v: string) => {
+      expect(featureSetForVersion(semver.parse(v)).wildcardSSH).toBeFalsy()
+    })
+    ;["v2.19.0", "v2.19.1", "v2.20.0+e491217", "v5.0.4+e491217"].forEach((v: string) => {
+      expect(featureSetForVersion(semver.parse(v)).wildcardSSH).toBeTruthy()
+    })
+  })
 })
diff --git a/src/featureSet.ts b/src/featureSet.ts
index 6d1195a6..892c66ef 100644
--- a/src/featureSet.ts
+++ b/src/featureSet.ts
@@ -22,6 +22,6 @@ export function featureSetForVersion(version: semver.SemVer | null): FeatureSet
     // If this check didn't exist, VS Code connections would fail on
     // older versions because of an unknown CLI argument.
     proxyLogDirectory: (version?.compare("2.3.3") || 0) > 0 || version?.prerelease[0] === "devel",
-    wildcardSSH: (version?.compare("2.19.0") || 0) > 0 || version?.prerelease[0] === "devel",
+    wildcardSSH: (version ? version.compare("2.19.0") : -1) >= 0 || version?.prerelease[0] === "devel",
   }
 }