diff --git a/lldb/include/lldb/DataFormatters/ValueObjectPrinter.h b/lldb/include/lldb/DataFormatters/ValueObjectPrinter.h
--- a/lldb/include/lldb/DataFormatters/ValueObjectPrinter.h
+++ b/lldb/include/lldb/DataFormatters/ValueObjectPrinter.h
@@ -98,7 +98,7 @@
 
   ValueObject *GetValueObjectForChildrenGeneration();
 
-  void PrintChildrenPreamble();
+  void PrintChildrenPreamble(bool value_printed, bool summary_printed);
 
   void PrintChildrenPostamble(bool print_dotdotdot);
 
diff --git a/lldb/source/DataFormatters/ValueObjectPrinter.cpp b/lldb/source/DataFormatters/ValueObjectPrinter.cpp
--- a/lldb/source/DataFormatters/ValueObjectPrinter.cpp
+++ b/lldb/source/DataFormatters/ValueObjectPrinter.cpp
@@ -445,7 +445,9 @@
       }
 
       if (m_summary.size()) {
-        m_stream->Printf(" %s", m_summary.c_str());
+        if (ShouldShowName() || value_printed)
+          m_stream->PutChar(' ');
+        m_stream->PutCString(m_summary);
         summary_printed = true;
       }
     }
@@ -560,7 +562,8 @@
   return m_valobj;
 }
 
-void ValueObjectPrinter::PrintChildrenPreamble() {
+void ValueObjectPrinter::PrintChildrenPreamble(bool value_printed,
+                                               bool summary_printed) {
   if (m_options.m_flat_output) {
     if (ShouldPrintValueObject())
       m_stream->EOL();
@@ -568,7 +571,7 @@
     if (ShouldPrintValueObject()) {
       if (IsRef()) {
         m_stream->PutCString(": ");
-      } else if (ShouldShowName()) {
+      } else if (value_printed || summary_printed || ShouldShowName()) {
         m_stream->PutChar(' ');
       }
       m_stream->PutCString("{\n");
@@ -694,7 +697,7 @@
     for (size_t idx = 0; idx < num_children; ++idx) {
       if (ValueObjectSP child_sp = GenerateChild(synth_m_valobj, idx)) {
         if (!any_children_printed) {
-          PrintChildrenPreamble();
+          PrintChildrenPreamble(value_printed, summary_printed);
           any_children_printed = true;
         }
         PrintChild(child_sp, curr_ptr_depth);
diff --git a/lldb/test/API/commands/dwim-print/TestDWIMPrint.py b/lldb/test/API/commands/dwim-print/TestDWIMPrint.py
--- a/lldb/test/API/commands/dwim-print/TestDWIMPrint.py
+++ b/lldb/test/API/commands/dwim-print/TestDWIMPrint.py
@@ -122,3 +122,12 @@
         self.runCmd("settings set auto-one-line-summaries false")
         self._expect_cmd(f"dwim-print s", "frame variable")
         self._expect_cmd(f"dwim-print (struct Structure)s", "expression")
+
+    def test_summary_strings(self):
+        """Test dwim-print with nested values (structs, etc)."""
+        self.build()
+        lldbutil.run_to_source_breakpoint(self, "// break here", lldb.SBFileSpec("main.c"))
+        self.runCmd("settings set auto-one-line-summaries false")
+        self.runCmd("type summary add -e -s 'stub summary' Structure")
+        self._expect_cmd(f"dwim-print s", "frame variable")
+        self._expect_cmd(f"dwim-print (struct Structure)s", "expression")