diff --git a/CHANGELOG.md b/CHANGELOG.md
index 8988ddb..cd981fe 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -2,6 +2,10 @@
 
 ## Unreleased
 
+### Fixed
+
+- SSH config is regenerated correctly when Workspaces are added or removed
+
 ## 0.1.0 - 2025-04-01
 
 ### Added
diff --git a/src/main/kotlin/com/coder/toolbox/CoderRemoteEnvironment.kt b/src/main/kotlin/com/coder/toolbox/CoderRemoteEnvironment.kt
index 62fe4bb..8319cdc 100644
--- a/src/main/kotlin/com/coder/toolbox/CoderRemoteEnvironment.kt
+++ b/src/main/kotlin/com/coder/toolbox/CoderRemoteEnvironment.kt
@@ -194,10 +194,9 @@ class CoderRemoteEnvironment(
      */
     override fun equals(other: Any?): Boolean {
         if (other == null) return false
-        if (this === other) return true // Note the triple ===
+        if (this === other) return true
         if (other !is CoderRemoteEnvironment) return false
-        if (id != other.id) return false
-        return true
+        return id == other.id
     }
 
     /**
diff --git a/src/main/kotlin/com/coder/toolbox/CoderRemoteProvider.kt b/src/main/kotlin/com/coder/toolbox/CoderRemoteProvider.kt
index fef85ff..4ce1bc7 100644
--- a/src/main/kotlin/com/coder/toolbox/CoderRemoteProvider.kt
+++ b/src/main/kotlin/com/coder/toolbox/CoderRemoteProvider.kt
@@ -113,12 +113,11 @@ class CoderRemoteProvider(
                     return@launch
                 }
 
-                // Reconfigure if a new environment is found.
-                // TODO@JB: Should we use the add/remove listeners instead?
-                val newEnvironments = resolvedEnvironments.subtract(lastEnvironments)
-                if (newEnvironments.isNotEmpty()) {
-                    context.logger.info("Found new environment(s), reconfiguring CLI: $newEnvironments")
-                    cli.configSsh(newEnvironments.map { it.name }.toSet())
+
+                // Reconfigure if environments changed.
+                if (lastEnvironments.size != resolvedEnvironments.size || lastEnvironments != resolvedEnvironments) {
+                    context.logger.info("Workspaces have changed, reconfiguring CLI: $resolvedEnvironments")
+                    cli.configSsh(resolvedEnvironments.map { it.name }.toSet())
                 }
 
                 environments.update {