diff --git a/gradle.properties b/gradle.properties
index 7277df2..f38cfba 100644
--- a/gradle.properties
+++ b/gradle.properties
@@ -1,5 +1,5 @@
 kotlin.code.style=official
-generexVersion=1.3.0
+generexVersion=1.4.0-SNAPSHOT
 
 POM_ARTIFACT_ID=generex
 POM_NAME=Generex
diff --git a/src/main/java/com/pkware/generex/Generex.java b/src/main/java/com/pkware/generex/Generex.java
index ef1939f..31de7b5 100644
--- a/src/main/java/com/pkware/generex/Generex.java
+++ b/src/main/java/com/pkware/generex/Generex.java
@@ -24,6 +24,7 @@
 import dk.brics.automaton.Transition;
 import org.jetbrains.annotations.NotNull;
 
+import java.util.ArrayDeque;
 import java.util.ArrayList;
 import java.util.Collection;
 import java.util.Collections;
@@ -62,15 +63,23 @@ public class Generex implements Iterable<String> {
     private boolean isTransactionNodeBuilt;
 
     /**
-     * Determined possible minimum and maximum length of a regex by traversing the
-     * Automaton tree using depth first search.
+     * Minimum length of any string this regex accepts. Populated on first access by
+     * {@link #calculateLengthBounds()}; {@code null} until then (doubles as the cache-populated flag).
      */
     private Integer cachedMinLength;
+
+    /**
+     * The regex's own upper bound on generated string length. Populated on first access by
+     * {@link #calculateLengthBounds()}. For infinite regexes this is {@link Integer#MAX_VALUE}
+     * (no natural cap) so that {@code Math.min(userMax, cachedMaxLength)} collapses to the user's
+     * value. Callers that need a default when the user supplied no max should use
+     * {@link #DEFAULT_INFINITE_MAX_LENGTH} instead for infinite regexes.
+     */
     private Integer cachedMaxLength;
 
     /**
-     * The maximum length a produced string for an infinite regex if {@link #random(int, int)} hasn't been given a max
-     * length other than {@link Integer#MAX_VALUE}.
+     * Fallback maximum length used by {@link #random(int)} (and overloads that delegate to it)
+     * when the regex is infinite and the caller did not supply their own {@code maxLength}.
      */
     public static final int DEFAULT_INFINITE_MAX_LENGTH = 50;
 
@@ -423,8 +432,10 @@ public String random() {
      */
     public String random(int minLength) {
         calculateLengthBounds();
-        int actualMaxLength = isInfinite() ? DEFAULT_INFINITE_MAX_LENGTH : cachedMaxLength;
-        return random(minLength, actualMaxLength);
+        // cachedMaxLength is Integer.MAX_VALUE for infinite regexes; fall back to the friendlier
+        // default since the caller didn't specify their own cap.
+        int defaultMaxLength = isInfinite() ? DEFAULT_INFINITE_MAX_LENGTH : cachedMaxLength;
+        return random(minLength, defaultMaxLength);
     }
 
     /**
@@ -451,9 +462,10 @@ public String random(int minLength) {
     public String random(int minLength, int maxLength) {
         calculateLengthBounds();
 
-        // Calculate actual valid range by comparing the regex and the user defined bounds
+        // Calculate actual valid range by comparing the regex and the user defined bounds.
+        // For infinite regexes cachedMaxLength is Integer.MAX_VALUE, so the min() leaves maxLength alone.
         int actualMinLength = Math.max(minLength, cachedMinLength);
-        int actualMaxLength = Math.min(maxLength, isInfinite() ? maxLength : cachedMaxLength);
+        int actualMaxLength = Math.min(maxLength, cachedMaxLength);
 
         // Pre-select target length uniformly from valid range
         int targetLength;
@@ -578,45 +590,96 @@ private String getBestMatch(String newMatch, String currentMatch, int min, int m
     }
 
     /**
-     * Calculate the possible bounds of the generated string by traversing the regex
+     * Calculate the possible bounds of the generated string by traversing the regex.
+     * <br>
+     * For finite automatons, both {@code cachedMinLength} and {@code cachedMaxLength} are populated
+     * from the DFS. For infinite automatons, {@code cachedMinLength} is computed from a BFS to the
+     * nearest accepting state, and {@code cachedMaxLength} is set to {@link Integer#MAX_VALUE}
+     * (meaning "no natural upper bound").
      */
     private void calculateLengthBounds() {
         if (cachedMinLength != null) return;
 
-        int[] bounds = dfsLengthBounds(automaton.getInitialState(), new HashSet<>());
-        cachedMinLength = bounds[0];
-        cachedMaxLength = bounds[1];
+        if (automaton.isFinite()) {
+            int[] bounds = dfsLengthBounds(automaton.getInitialState(), new HashMap<>());
+            cachedMinLength = bounds[0];
+            cachedMaxLength = bounds[1];
+        } else {
+            cachedMinLength = bfsMinLength(automaton.getInitialState());
+            cachedMaxLength = Integer.MAX_VALUE;
+        }
     }
 
     /**
-     * Uses a depth first search to calculate the minimum and maximum length of the regex by
-     * traversing through the automaton tree.
+     * Uses a memoized depth first search to calculate the minimum and maximum length of the regex
+     * by traversing through the automaton.
      * <br>
-     * We can use DFS because the automaton is finite (does not contain infinite loops) and
-     * we need to visit every state regardless to determine the longest length.
+     * Assumes the automaton is finite (acyclic). Under that assumption each state's bounds depend
+     * only on the state itself, so results can be cached in {@code memo}. Without memoization,
+     * automatons shaped like a chain of states with multiple parallel transitions (e.g.
+     * {@code [a-zA-Z0-9]{1,100}}, which determinizes to ~3 range-transitions per state) would be
+     * explored along every path — exponential in the chain length. Memoization makes this linear
+     * in the number of states.
      *
      * @param state the current state of the automaton.
-     * @param visited the set of visited states.
+     * @param memo  cached bounds for states whose subtree has already been computed.
      * @return an int array containing the minimum and maximum length of the regex.
      */
-    private int[] dfsLengthBounds(State state, Set<State> visited) {
-        if (visited.contains(state)) return new int[]{Integer.MAX_VALUE, 0};
+    private int[] dfsLengthBounds(State state, Map<State, int[]> memo) {
+        int[] cached = memo.get(state);
+        if (cached != null) return cached;
 
         int minLength = state.isAccept() ? 0 : Integer.MAX_VALUE;
         int maxLength = 0;
 
-        visited.add(state);
-
         for (Transition transition : state.getTransitions()) {
-            int[] bounds = dfsLengthBounds(transition.getDest(), visited);
+            int[] bounds = dfsLengthBounds(transition.getDest(), memo);
             if (bounds[0] != Integer.MAX_VALUE) {
                 minLength = Math.min(minLength, bounds[0] + 1);
             }
             maxLength = Math.max(maxLength, bounds[1] + 1);
         }
 
-        visited.remove(state);
-        return new int[]{minLength, maxLength};
+        int[] result = {minLength, maxLength};
+        memo.put(state, result);
+        return result;
+    }
+
+    /**
+     * Computes the minimum length of any string the automaton accepts, via a breadth-first search
+     * from {@code initial} to the nearest accepting state.
+     * <br>
+     * Used for infinite (cyclic) automatons where the acyclic-memoized DFS assumption does not
+     * hold. Returns {@code 0} if {@code initial} itself is accepting. Returns
+     * {@link Integer#MAX_VALUE} if no accepting state is reachable (not expected for a valid regex).
+     *
+     * @param initial the state to search from.
+     * @return the shortest number of transitions needed to reach an accepting state.
+     */
+    private int bfsMinLength(State initial) {
+        Set<State> visited = new HashSet<>();
+        ArrayDeque<State> currentLevel = new ArrayDeque<>();
+        ArrayDeque<State> nextLevel = new ArrayDeque<>();
+
+        currentLevel.add(initial);
+        visited.add(initial);
+
+        int depth = 0;
+        while (!currentLevel.isEmpty()) {
+            for (State state : currentLevel) {
+                if (state.isAccept()) return depth;
+                for (Transition transition : state.getTransitions()) {
+                    State dest = transition.getDest();
+                    if (visited.add(dest)) nextLevel.add(dest);
+                }
+            }
+            ArrayDeque<State> tmp = currentLevel;
+            currentLevel = nextLevel;
+            nextLevel = tmp;
+            nextLevel.clear();
+            depth++;
+        }
+        return Integer.MAX_VALUE;
     }
 
     /**
diff --git a/src/test/kotlin/com/pkware/generex/KotlinTests.kt b/src/test/kotlin/com/pkware/generex/KotlinTests.kt
index 0dfaf8e..7600639 100644
--- a/src/test/kotlin/com/pkware/generex/KotlinTests.kt
+++ b/src/test/kotlin/com/pkware/generex/KotlinTests.kt
@@ -265,6 +265,24 @@ class KotlinTests {
         assertThat(generex.random()).isEqualTo("hello\\")
     }
 
+    @ParameterizedTest
+    @MethodSource("longRegexes")
+    fun `generating from long bounded regexes does not hang`(regex: String) {
+        val generex = Generex(regex)
+        val times = mutableListOf<Long>()
+
+        repeat(100) {
+            val start = System.nanoTime()
+            val result = generex.random()
+            times.add(System.nanoTime() - start)
+
+            assertThat(result).matches(regex)
+        }
+
+        val averageMs = times.average() / 1_000_000
+        assertThat(averageMs).isLessThan(100.0)
+    }
+
     companion object {
 
         @JvmStatic
@@ -326,5 +344,11 @@ class KotlinTests {
             Arguments.of("aaa", 2),
             Arguments.of("a{5,10}", 2),
         )
+
+        @JvmStatic
+        fun longRegexes() = Stream.of(
+            Arguments.of("[a-zA-Z0-9]{1,100}"),
+            Arguments.of("[a-zA-Z0-9]{1,200}"),
+        )
     }
 }