diff --git a/expression/src/main/java/io/smallrye/common/expression/Expression.java b/expression/src/main/java/io/smallrye/common/expression/Expression.java
index 555a04d..a42554c 100644
--- a/expression/src/main/java/io/smallrye/common/expression/Expression.java
+++ b/expression/src/main/java/io/smallrye/common/expression/Expression.java
@@ -195,6 +195,10 @@ static final class Itr {
             this.str = str;
         }
 
+        boolean hasPrev() {
+            return idx > 0;
+        }
+
         boolean hasNext() {
             return idx < str.length();
         }
@@ -258,6 +262,25 @@ private static Node parseString(Itr itr, final boolean allowExpr, final boolean
                         // treat as plain content
                         continue;
                     }
+                    if (flags.contains(Flag.STRICT_ESCAPES)) {
+                        if (!itr.hasNext()) {
+                            continue;
+                        } else if (itr.peekNext() == '$') {
+                            list.add(new LiteralNode(itr.getStr(), start, itr.getNextIdx()));
+                            start = itr.getNextIdx();
+                            continue;
+                        } else if (itr.peekNext() != '{') {
+                            continue;
+                        } else if (itr.hasPrev()) {
+                            itr.prev();
+                            if (itr.hasPrev() && itr.peekPrev() == '$') {
+                                itr.next();
+                                start = itr.getNextIdx();
+                                continue;
+                            }
+                            itr.next();
+                        }
+                    }
                     // check to see if it's a dangling $
                     if (!itr.hasNext()) {
                         if (!flags.contains(Flag.LENIENT_SYNTAX)) {
@@ -614,6 +637,21 @@ private static Node parseString(Itr itr, final boolean allowExpr, final boolean
                             start = itr.getNextIdx();
                             continue;
                         }
+                    } else if (flags.contains(Flag.STRICT_ESCAPES)) {
+                        int escape = itr.getNextIdx();
+                        if (itr.hasNext() && itr.peekNext() == '$') {
+                            itr.next();
+                            if (itr.hasNext() && itr.peekNext() == '{') {
+                                list.add(new LiteralNode(itr.getStr(), start, escape - 1));
+                                list.add(new LiteralNode(itr.getStr(), escape, itr.getNextIdx()));
+                                start = itr.getNextIdx();
+                            } else if (itr.hasNext() && itr.peekNext() == '$') {
+                                list.add(new LiteralNode(itr.getStr(), start, escape));
+                                start = itr.getPrevIdx();
+                                itr.prev();
+                            }
+                        }
+                        continue;
                     }
                     // TP 42
                     // otherwise, just...
@@ -694,6 +732,11 @@ public enum Flag {
          * character.
          */
         ESCAPES,
+        /**
+         * Escaping <code>$</code> with <code>$$</code> or <code>/$</code> only applies when <code>{</code> follows
+         * the initial escaped <code>$</code>.
+         */
+        STRICT_ESCAPES,
         /**
          * Treat expressions containing a double-colon delimiter as special, encoding the entire content into the key.
          */
diff --git a/expression/src/test/java/io/smallrye/common/expression/ExpressionTestCase.java b/expression/src/test/java/io/smallrye/common/expression/ExpressionTestCase.java
index 53046ca..0a32038 100644
--- a/expression/src/test/java/io/smallrye/common/expression/ExpressionTestCase.java
+++ b/expression/src/test/java/io/smallrye/common/expression/ExpressionTestCase.java
@@ -693,4 +693,98 @@ void expressions() {
             b.append(c.getExpandedDefault());
         }));
     }
+
+    @Test
+    void strictEscapes() {
+        assertEquals("$", Expression.compile("$", STRICT_ESCAPES).evaluate((c, b) -> {
+        }));
+        assertEquals("$$", Expression.compile("$$", STRICT_ESCAPES).evaluate((c, b) -> {
+        }));
+        assertEquals("\\$", Expression.compile("\\$", STRICT_ESCAPES).evaluate((c, b) -> {
+        }));
+        assertEquals("\\$$", Expression.compile("\\$$", STRICT_ESCAPES).evaluate((c, b) -> {
+        }));
+        assertEquals("$$foo", Expression.compile("$$foo", STRICT_ESCAPES).evaluate((c, b) -> {
+        }));
+        assertEquals("foo$$", Expression.compile("foo$$", STRICT_ESCAPES).evaluate((c, b) -> {
+        }));
+        assertEquals("$$foo", Expression.compile("$$foo", STRICT_ESCAPES).evaluate((c, b) -> {
+        }));
+        assertEquals("foo$$bar", Expression.compile("foo$$bar", STRICT_ESCAPES).evaluate((c, b) -> {
+        }));
+        assertEquals("${foo}", Expression.compile("$${foo}", STRICT_ESCAPES).evaluate((c, b) -> {
+        }));
+        assertEquals("$${foo}", Expression.compile("$$${foo}", STRICT_ESCAPES).evaluate((c, b) -> {
+        }));
+        assertEquals("$${foo}$", Expression.compile("$$${foo}$", STRICT_ESCAPES).evaluate((c, b) -> {
+        }));
+        assertEquals("$${foo}$$", Expression.compile("$$${foo}$$", STRICT_ESCAPES).evaluate((c, b) -> {
+        }));
+        assertEquals("foo${bar}", Expression.compile("foo$${bar}", STRICT_ESCAPES).evaluate((c, b) -> {
+        }));
+        assertEquals("foo$${bar}", Expression.compile("foo$$${bar}", STRICT_ESCAPES).evaluate((c, b) -> {
+        }));
+        assertEquals("foo$$$${bar}", Expression.compile("foo$$$$${bar}", STRICT_ESCAPES).evaluate((c, b) -> {
+        }));
+        assertEquals("foo$$$${bar}$$$baz", Expression.compile("foo$$$$${bar}$$$baz", STRICT_ESCAPES).evaluate((c, b) -> {
+        }));
+        assertEquals("foo$$$$", Expression.compile("foo$$$$", STRICT_ESCAPES).evaluate((c, b) -> {
+        }));
+        assertEquals("${foo:bar}", Expression.compile("$${foo:bar}", STRICT_ESCAPES).evaluate((c, b) -> {
+        }));
+        assertEquals("$${foo:bar}", Expression.compile("$$${foo:bar}", STRICT_ESCAPES).evaluate((c, b) -> {
+        }));
+        assertEquals("${foo:}", Expression.compile("$${foo:${bar}}", STRICT_ESCAPES).evaluate((c, b) -> {
+        }));
+        assertEquals("${foo:${bar}}", Expression.compile("$${foo:$${bar}}", STRICT_ESCAPES).evaluate((c, b) -> {
+        }));
+
+        assertEquals("", Expression.compile("${foo}", STRICT_ESCAPES).evaluate((c, b) -> {
+            assertEquals("foo", c.getKey());
+        }));
+        assertEquals("", Expression.compile("${foo}${bar}", STRICT_ESCAPES).evaluate((c, b) -> {
+            if ("foo".equals(c.getKey()))
+                assertEquals("foo", c.getKey());
+            if ("bar".equals(c.getKey()))
+                assertEquals("bar", c.getKey());
+        }));
+        assertEquals("foobar", Expression.compile("foo${foo}${bar}bar", STRICT_ESCAPES).evaluate((c, b) -> {
+            if ("foo".equals(c.getKey()))
+                assertEquals("foo", c.getKey());
+            if ("bar".equals(c.getKey()))
+                assertEquals("bar", c.getKey());
+        }));
+        assertEquals("foo${foo}bar", Expression.compile("foo$${foo}${bar}bar", STRICT_ESCAPES).evaluate((c, b) -> {
+            if ("bar".equals(c.getKey()))
+                assertEquals("bar", c.getKey());
+        }));
+        assertEquals("foo${foo}bar", Expression.compile("foo$${foo${bar}}bar", STRICT_ESCAPES).evaluate((c, b) -> {
+            if ("bar".equals(c.getKey()))
+                assertEquals("bar", c.getKey());
+        }));
+        assertEquals("", Expression.compile("${}", STRICT_ESCAPES).evaluate((c, b) -> {
+            assertEquals("", c.getKey());
+        }));
+        assertEquals("", Expression.compile("${:}", STRICT_ESCAPES).evaluate((c, b) -> {
+            assertEquals("", c.getKey());
+        }));
+
+        assertEquals("${foo}", Expression.compile("\\${foo}", STRICT_ESCAPES).evaluate((c, b) -> {
+        }));
+        assertEquals("${foo}bar", Expression.compile("\\${foo}bar", STRICT_ESCAPES).evaluate((c, b) -> {
+        }));
+        assertEquals("\\$\\{%s}", Expression.compile("\\$\\{%s}", STRICT_ESCAPES).evaluate((c, b) -> {
+        }));
+        assertEquals("foo${bar}", Expression.compile("foo\\${bar}", STRICT_ESCAPES).evaluate((c, b) -> {
+        }));
+        assertEquals("foo\\${bar}", Expression.compile("foo\\\\${bar}", STRICT_ESCAPES).evaluate((c, b) -> {
+        }));
+
+        assertEquals("foo\\${bar}", Expression.compile("foo\\$${bar}", STRICT_ESCAPES).evaluate((c, b) -> {
+        }));
+        assertEquals("foo$${bar}", Expression.compile("foo$\\${bar}", STRICT_ESCAPES).evaluate((c, b) -> {
+        }));
+        assertEquals("foo$$\\{bar}", Expression.compile("foo$$\\{bar}", STRICT_ESCAPES).evaluate((c, b) -> {
+        }));
+    }
 }