diff --git a/lldb/include/lldb/DataFormatters/DumpValueObjectOptions.h b/lldb/include/lldb/DataFormatters/DumpValueObjectOptions.h
--- a/lldb/include/lldb/DataFormatters/DumpValueObjectOptions.h
+++ b/lldb/include/lldb/DataFormatters/DumpValueObjectOptions.h
@@ -102,6 +102,8 @@
 
   DumpValueObjectOptions &SetHideRootType(bool hide_root_type = false);
 
+  DumpValueObjectOptions &SetHideRootName(bool hide_root_name);
+
   DumpValueObjectOptions &SetHideName(bool hide_name = false);
 
   DumpValueObjectOptions &SetHideValue(bool hide_value = false);
@@ -143,6 +145,7 @@
   bool m_show_location : 1;
   bool m_use_objc : 1;
   bool m_hide_root_type : 1;
+  bool m_hide_root_name : 1;
   bool m_hide_name : 1;
   bool m_hide_value : 1;
   bool m_run_validator : 1;
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
@@ -120,6 +120,8 @@
   bool HasReachedMaximumDepth();
 
 private:
+  bool ShouldShowName() const;
+
   ValueObject *m_orig_valobj;
   ValueObject *m_valobj;
   Stream *m_stream;
diff --git a/lldb/source/Commands/CommandObjectDWIMPrint.cpp b/lldb/source/Commands/CommandObjectDWIMPrint.cpp
--- a/lldb/source/Commands/CommandObjectDWIMPrint.cpp
+++ b/lldb/source/Commands/CommandObjectDWIMPrint.cpp
@@ -88,7 +88,7 @@
 
   DumpValueObjectOptions dump_options = m_varobj_options.GetAsDumpOptions(
       m_expr_options.m_verbosity, m_format_options.GetFormat());
-  dump_options.SetHideName(eval_options.GetSuppressPersistentResult());
+  dump_options.SetHideRootName(eval_options.GetSuppressPersistentResult());
 
   // First, try `expr` as the name of a frame variable.
   if (StackFrame *frame = m_exe_ctx.GetFramePtr()) {
diff --git a/lldb/source/Commands/CommandObjectExpression.cpp b/lldb/source/Commands/CommandObjectExpression.cpp
--- a/lldb/source/Commands/CommandObjectExpression.cpp
+++ b/lldb/source/Commands/CommandObjectExpression.cpp
@@ -456,7 +456,7 @@
 
         DumpValueObjectOptions options(m_varobj_options.GetAsDumpOptions(
             m_command_options.m_verbosity, format));
-        options.SetHideName(eval_options.GetSuppressPersistentResult());
+        options.SetHideRootName(eval_options.GetSuppressPersistentResult());
         options.SetVariableFormatDisplayLanguage(
             result_valobj_sp->GetPreferredDisplayLanguage());
 
diff --git a/lldb/source/DataFormatters/DumpValueObjectOptions.cpp b/lldb/source/DataFormatters/DumpValueObjectOptions.cpp
--- a/lldb/source/DataFormatters/DumpValueObjectOptions.cpp
+++ b/lldb/source/DataFormatters/DumpValueObjectOptions.cpp
@@ -19,10 +19,10 @@
       m_decl_printing_helper(), m_pointer_as_array(), m_use_synthetic(true),
       m_scope_already_checked(false), m_flat_output(false), m_ignore_cap(false),
       m_show_types(false), m_show_location(false), m_use_objc(false),
-      m_hide_root_type(false), m_hide_name(false), m_hide_value(false),
-      m_run_validator(false), m_use_type_display_name(true),
-      m_allow_oneliner_mode(true), m_hide_pointer_value(false),
-      m_reveal_empty_aggregates(true) {}
+      m_hide_root_type(false), m_hide_root_name(false), m_hide_name(false),
+      m_hide_value(false), m_run_validator(false),
+      m_use_type_display_name(true), m_allow_oneliner_mode(true),
+      m_hide_pointer_value(false), m_reveal_empty_aggregates(true) {}
 
 DumpValueObjectOptions::DumpValueObjectOptions(ValueObject &valobj)
     : DumpValueObjectOptions() {
@@ -143,6 +143,12 @@
   return *this;
 }
 
+DumpValueObjectOptions &
+DumpValueObjectOptions::SetHideRootName(bool hide_root_name) {
+  m_hide_root_name = hide_root_name;
+  return *this;
+}
+
 DumpValueObjectOptions &DumpValueObjectOptions::SetHideName(bool hide_name) {
   m_hide_name = hide_name;
   return *this;
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
@@ -275,7 +275,7 @@
 
   StreamString varName;
 
-  if (!m_options.m_hide_name) {
+  if (ShouldShowName()) {
     if (m_options.m_flat_output)
       m_valobj->GetExpressionPath(varName);
     else
@@ -314,7 +314,7 @@
       m_stream->Printf("(%s) ", typeName.GetData());
     if (!varName.Empty())
       m_stream->Printf("%s =", varName.GetData());
-    else if (!m_options.m_hide_name)
+    else if (ShouldShowName())
       m_stream->Printf(" =");
   }
 }
@@ -437,7 +437,7 @@
         if (m_options.m_hide_pointer_value &&
             IsPointerValue(m_valobj->GetCompilerType())) {
         } else {
-          if (!m_options.m_hide_name)
+          if (ShouldShowName())
             m_stream->PutChar(' ');
           m_stream->PutCString(m_value);
           value_printed = true;
@@ -459,7 +459,7 @@
     // let's avoid the overly verbose no description error for a nil thing
     if (m_options.m_use_objc && !IsNil() && !IsUninitialized() &&
         (!m_options.m_pointer_as_array)) {
-      if (!m_options.m_hide_value || !m_options.m_hide_name)
+      if (!m_options.m_hide_value || ShouldShowName())
         m_stream->Printf(" ");
       const char *object_desc = nullptr;
       if (value_printed || summary_printed)
@@ -565,8 +565,14 @@
     if (ShouldPrintValueObject())
       m_stream->EOL();
   } else {
-    if (ShouldPrintValueObject())
-      m_stream->PutCString(IsRef() ? ": {\n" : " {\n");
+    if (ShouldPrintValueObject()) {
+      if (IsRef()) {
+        m_stream->PutCString(": ");
+      } else if (ShouldShowName()) {
+        m_stream->PutChar(' ');
+      }
+      m_stream->PutCString("{\n");
+    }
     m_stream->IndentMore();
   }
 }
@@ -819,3 +825,9 @@
 bool ValueObjectPrinter::HasReachedMaximumDepth() {
   return m_curr_depth >= m_options.m_max_depth;
 }
+
+bool ValueObjectPrinter::ShouldShowName() const {
+  if (m_curr_depth == 0)
+    return !m_options.m_hide_root_name && !m_options.m_hide_name;
+  return !m_options.m_hide_name;
+}
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
@@ -114,3 +114,11 @@
         error_msg = "error: 'dwim-print' takes a variable or expression"
         self.expect(f"dwim-print", error=True, startstr=error_msg)
         self.expect(f"dwim-print -- ", error=True, startstr=error_msg)
+
+    def test_nested_values(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._expect_cmd(f"dwim-print s", "frame variable")
+        self._expect_cmd(f"dwim-print (struct Structure)s", "expression")
diff --git a/lldb/test/API/commands/dwim-print/main.c b/lldb/test/API/commands/dwim-print/main.c
--- a/lldb/test/API/commands/dwim-print/main.c
+++ b/lldb/test/API/commands/dwim-print/main.c
@@ -1,3 +1,10 @@
+struct Structure {
+  int number;
+};
+
 int main(int argc, char **argv) {
+  struct Structure s;
+  s.number = 30;
+  // break here
   return 0;
 }