diff --git a/source/dub/dub.d b/source/dub/dub.d
index a18857d..403d3e4 100644
--- a/source/dub/dub.d
+++ b/source/dub/dub.d
@@ -1084,11 +1084,22 @@
 				continue;
 			}
 
-			if (dspec.optional && !m_dub.packageManager.getFirstPackage(dname))
-				continue;
-			if (m_options & UpgradeOptions.upgrade || !m_selectedVersions || !m_selectedVersions.hasSelectedVersion(dbasename))
-				ret ~= TreeNodes(dname, dspec.mapToPath(pack.path));
-			else ret ~= TreeNodes(dname, m_selectedVersions.getSelectedVersion(dbasename));
+			DependencyType dt;
+			if (dspec.optional) {
+				if (dspec.default_) dt = DependencyType.optionalDefault;
+				else dt = DependencyType.optional;
+			} else dt = DependencyType.required;
+
+			if (m_options & UpgradeOptions.upgrade || !m_selectedVersions || !m_selectedVersions.hasSelectedVersion(dbasename)) {
+				// keep deselected dependencies deselected by default
+				if (m_selectedVersions && !m_selectedVersions.bare && dt == DependencyType.optionalDefault)
+					dt = DependencyType.optional;
+				ret ~= TreeNodes(dname, dspec.mapToPath(pack.path), dt);
+			} else {
+				// keep already selected optional dependencies if possible
+				if (dt == DependencyType.optional) dt = DependencyType.optionalDefault;
+				ret ~= TreeNodes(dname, m_selectedVersions.getSelectedVersion(dbasename), dt);
+			}
 		}
 		return ret.data;
 	}
diff --git a/source/dub/project.d b/source/dub/project.d
index dfb75e4..bc5bcce 100644
--- a/source/dub/project.d
+++ b/source/dub/project.d
@@ -1230,6 +1230,7 @@
 		enum FileVersion = 1;
 		Selected[string] m_selections;
 		bool m_dirty = false; // has changes since last save
+		bool m_bare = true;
 	}
 
 	enum defaultFile = "dub.selections.json";
@@ -1247,12 +1248,16 @@
 		auto json = jsonFromFile(path);
 		deserialize(json);
 		m_dirty = false;
+		m_bare = false;
 	}
 
 	@property string[] selectedPackages() const { return m_selections.keys; }
 
 	@property bool dirty() const { return m_dirty; }
 
+	/// Determine if this set of selections is empty and has not been saved to disk.
+	@property bool bare() const { return m_bare && !m_dirty; }
+
 	void clear()
 	{
 		m_selections = null;
@@ -1310,6 +1315,7 @@
 		file.writePrettyJsonString(json);
 		file.put('\n');
 		m_dirty = false;
+		m_bare = false;
 	}
 
 	static Json dependencyToJson(Dependency d)