diff --git a/core/ast.h b/core/ast.h
index 9bcf94890..a21221e0a 100644
--- a/core/ast.h
+++ b/core/ast.h
@@ -586,7 +586,7 @@ struct LiteralNumber : public AST {
 /** Represents JSON strings. */
 struct LiteralString : public AST {
     UString value;
-    enum TokenKind { SINGLE, DOUBLE, BLOCK, VERBATIM_SINGLE, VERBATIM_DOUBLE };
+    enum TokenKind { SINGLE, DOUBLE, BLOCK, VERBATIM_SINGLE, VERBATIM_DOUBLE, RAW_DESUGARED };
     TokenKind tokenKind;
     std::string blockIndent;      // Only contains ' ' and '\t'.
     std::string blockTermIndent;  // Only contains ' ' and '\t'.
diff --git a/core/desugarer.cpp b/core/desugarer.cpp
index 625e3b475..5fd9acfd5 100644
--- a/core/desugarer.cpp
+++ b/core/desugarer.cpp
@@ -119,12 +119,12 @@ class Desugarer {
 
     LiteralString *str(const UString &s)
     {
-        return make<LiteralString>(E, EF, s, LiteralString::DOUBLE, "", "");
+        return make<LiteralString>(E, EF, s, LiteralString::RAW_DESUGARED, "", "");
     }
 
     LiteralString *str(const LocationRange &loc, const UString &s)
     {
-        return make<LiteralString>(loc, EF, s, LiteralString::DOUBLE, "", "");
+        return make<LiteralString>(loc, EF, s, LiteralString::RAW_DESUGARED, "", "");
     }
 
     LiteralNull *null(void)
@@ -851,12 +851,13 @@ class Desugarer {
             // Nothing to do.
 
         } else if (auto *ast = dynamic_cast<LiteralString *>(ast_)) {
-            if ((ast->tokenKind != LiteralString::BLOCK) &&
+            if ((ast->tokenKind != LiteralString::RAW_DESUGARED) &&
+                (ast->tokenKind != LiteralString::BLOCK) &&
                 (ast->tokenKind != LiteralString::VERBATIM_DOUBLE) &&
                 (ast->tokenKind != LiteralString::VERBATIM_SINGLE)) {
                 ast->value = jsonnet_string_unescape(ast->location, ast->value);
             }
-            ast->tokenKind = LiteralString::DOUBLE;
+            ast->tokenKind = LiteralString::RAW_DESUGARED;
             ast->blockIndent.clear();
 
         } else if (dynamic_cast<const LiteralNull *>(ast_)) {
diff --git a/core/formatter.cpp b/core/formatter.cpp
index a17483556..cad3369c1 100644
--- a/core/formatter.cpp
+++ b/core/formatter.cpp
@@ -490,6 +490,7 @@ class Unparser {
             o << ast->originalString;
 
         } else if (auto *ast = dynamic_cast<const LiteralString *>(ast_)) {
+            assert(ast->tokenKind != LiteralString::RAW_DESUGARED);
             if (ast->tokenKind == LiteralString::DOUBLE) {
                 o << "\"";
                 o << encode_utf8(ast->value);
@@ -647,6 +648,7 @@ class EnforceStringStyle : public FmtPass {
     EnforceStringStyle(Allocator &alloc, const FmtOpts &opts) : FmtPass(alloc, opts) {}
     void visit(LiteralString *lit)
     {
+        assert(lit->tokenKind != LiteralString::RAW_DESUGARED);
         if (lit->tokenKind == LiteralString::BLOCK)
             return;
         if (lit->tokenKind == LiteralString::VERBATIM_DOUBLE)
@@ -1881,6 +1883,7 @@ class FixIndentation {
             column += ast->originalString.length();
 
         } else if (auto *ast = dynamic_cast<LiteralString *>(ast_)) {
+            assert(ast->tokenKind != LiteralString::RAW_DESUGARED);
             if (ast->tokenKind == LiteralString::DOUBLE) {
                 column += 2 + ast->value.length();  // Include quotes
             } else if (ast->tokenKind == LiteralString::SINGLE) {
diff --git a/core/libjsonnet.cpp b/core/libjsonnet.cpp
index 5bd92157e..730cef8e7 100644
--- a/core/libjsonnet.cpp
+++ b/core/libjsonnet.cpp
@@ -35,6 +35,8 @@ extern "C" {
 #include "parser.h"
 #include "static_analysis.h"
 #include "vm.h"
+#include "pass.h"
+#include "string_utils.h"
 
 namespace {
 using ::jsonnet::internal::Allocator;
@@ -42,12 +44,40 @@ using ::jsonnet::internal::AST;
 using ::jsonnet::internal::FmtOpts;
 using ::jsonnet::internal::Fodder;
 using ::jsonnet::internal::jsonnet_lex;
+using ::jsonnet::internal::jsonnet_string_escape;
 using ::jsonnet::internal::RuntimeError;
 using ::jsonnet::internal::StaticError;
 using ::jsonnet::internal::Tokens;
 using ::jsonnet::internal::VmExt;
 using ::jsonnet::internal::VmNativeCallback;
 using ::jsonnet::internal::VmNativeCallbackMap;
+using ::jsonnet::internal::CompilerPass;
+using ::jsonnet::internal::LiteralString;
+
+// Used in fmtDebugDesugaring mode to ensure the AST can be pretty-printed.
+class ReEscapeStrings : public CompilerPass {
+    using CompilerPass::visit;
+  public:
+    ReEscapeStrings(Allocator &alloc) : CompilerPass(alloc) {}
+    void visit(LiteralString *lit)
+    {
+        if (lit->tokenKind != LiteralString::RAW_DESUGARED)
+            return;
+
+        // TODO: Share code with formatter.cpp EnforceStringStyle.
+        unsigned num_single = 0, num_double = 0;
+        for (char32_t c : lit->value) {
+            if (c == '\'')
+                num_single++;
+            if (c == '"')
+                num_double++;
+        }
+        bool use_single = (num_double > 0) && (num_single == 0);
+
+        lit->value = jsonnet_string_escape(lit->value, use_single);
+        lit->tokenKind = use_single ? LiteralString::SINGLE : LiteralString::DOUBLE;
+    }
+};
 }  // namespace
 
 static void memory_panic(void)
@@ -450,8 +480,10 @@ static char *jsonnet_fmt_snippet_aux(JsonnetVm *vm, const char *filename, const
         expr = jsonnet_parse(&alloc, tokens);
         Fodder final_fodder = tokens.front().fodder;
 
-        if (vm->fmtDebugDesugaring)
+        if (vm->fmtDebugDesugaring) {
             jsonnet_desugar(&alloc, expr, &vm->tla);
+            ReEscapeStrings(alloc).expr(expr);
+        }
 
         json_str = jsonnet_fmt(expr, final_fodder, vm->fmtOpts);