diff --git a/src/main/java/org/apache/commons/cli/DefaultParser.java b/src/main/java/org/apache/commons/cli/DefaultParser.java
index 9f9285d78..6bd5bb391 100644
--- a/src/main/java/org/apache/commons/cli/DefaultParser.java
+++ b/src/main/java/org/apache/commons/cli/DefaultParser.java
@@ -518,16 +518,16 @@ private void handleProperties(final Properties properties) throws ParseException
             if (!cmd.hasOption(option) && !selected) {
                 // get the value from the properties
                 final String value = properties.getProperty(option);
-
-                if (opt.hasArg()) {
-                    if (opt.isValuesEmpty()) {
-                        opt.processValue(stripLeadingAndTrailingQuotesDefaultOff(value));
-                    }
-                } else if (!("yes".equalsIgnoreCase(value) || "true".equalsIgnoreCase(value) || "1".equalsIgnoreCase(value))) {
+                if (!opt.hasArg() && !("yes".equalsIgnoreCase(value) || "true".equalsIgnoreCase(value) || "1".equalsIgnoreCase(value))) {
                     // if the value is not yes, true or 1 then don't add the option to the CommandLine
                     continue;
                 }
-                handleOption(opt);
+                // the Options belong to the caller and outlive this parse, so hold the value on a copy
+                final Option copy = (Option) opt.clone();
+                if (copy.hasArg() && copy.isValuesEmpty()) {
+                    copy.processValue(stripLeadingAndTrailingQuotesDefaultOff(value));
+                }
+                handleOption(copy);
                 currentOption = null;
             }
         }
diff --git a/src/main/java/org/apache/commons/cli/Parser.java b/src/main/java/org/apache/commons/cli/Parser.java
index d120ea212..c1ef4374c 100644
--- a/src/main/java/org/apache/commons/cli/Parser.java
+++ b/src/main/java/org/apache/commons/cli/Parser.java
@@ -284,21 +284,22 @@ protected void processProperties(final Properties properties) throws ParseExcept
             if (!cmd.hasOption(option) && !selected) {
                 // get the value from the properties instance
                 final String value = properties.getProperty(option);
-                if (opt.hasArg()) {
-                    if (opt.isValuesEmpty()) {
-                        try {
-                            opt.processValue(value);
-                        } catch (final RuntimeException exp) { // NOPMD
-                            // if we cannot add the value don't worry about it
-                        }
-                    }
-                } else if (!("yes".equalsIgnoreCase(value) || "true".equalsIgnoreCase(value) || "1".equalsIgnoreCase(value))) {
+                if (!opt.hasArg() && !("yes".equalsIgnoreCase(value) || "true".equalsIgnoreCase(value) || "1".equalsIgnoreCase(value))) {
                     // if the value is not yes, true or 1 then don't add the
                     // option to the CommandLine
                     continue;
                 }
-                cmd.addOption(opt);
-                updateRequiredOptions(opt);
+                // the Options belong to the caller and outlive this parse, so hold the value on a copy
+                final Option copy = (Option) opt.clone();
+                if (copy.hasArg() && copy.isValuesEmpty()) {
+                    try {
+                        copy.processValue(value);
+                    } catch (final RuntimeException exp) { // NOPMD
+                        // if we cannot add the value don't worry about it
+                    }
+                }
+                cmd.addOption(copy);
+                updateRequiredOptions(copy);
             }
         }
     }
diff --git a/src/test/java/org/apache/commons/cli/AbstractParserTestCase.java b/src/test/java/org/apache/commons/cli/AbstractParserTestCase.java
index 58657821a..a131046bf 100644
--- a/src/test/java/org/apache/commons/cli/AbstractParserTestCase.java
+++ b/src/test/java/org/apache/commons/cli/AbstractParserTestCase.java
@@ -616,6 +616,26 @@ void testPropertyOptionRequired() throws Exception {
         assertTrue(cmd.hasOption("f"));
     }
 
+    @Test
+    void testPropertyOptionReusedOptions() throws Exception {
+        final Options options = new Options();
+        options.addOption(Option.builder("k").hasArg().get());
+
+        final Properties first = new Properties();
+        first.setProperty("k", "one");
+        final CommandLine firstCmd = parse(parser, options, null, first);
+        assertEquals("one", firstCmd.getOptionValue('k'));
+
+        final Properties second = new Properties();
+        second.setProperty("k", "two");
+        final CommandLine secondCmd = parse(parser, options, null, second);
+        assertEquals("two", secondCmd.getOptionValue('k'));
+
+        // the second parse must not reach back into the first result, and the Options must be left alone
+        assertEquals("one", firstCmd.getOptionValue('k'));
+        assertNull(options.getOption("k").getValue());
+    }
+
     @Test
     void testPropertyOptionSingularValue() throws Exception {
         final Options options = new Options();