diff --git a/src/pathops/SkIntersections.cpp b/src/pathops/SkIntersections.cpp
index fd65088..26ac479 100644
--- a/src/pathops/SkIntersections.cpp
+++ b/src/pathops/SkIntersections.cpp
@@ -45,7 +45,12 @@ int SkIntersections::insert(double one, double two, const SkDPoint& pt) {
         if (one == oldOne && two == oldTwo) {
             return -1;
         }
-        if (more_roughly_equal(oldOne, one) && more_roughly_equal(oldTwo, two)) {
+        // Check if T values are close enough to merge
+        bool tValuesClose = more_roughly_equal(oldOne, one) && more_roughly_equal(oldTwo, two);
+        // Check if coordinates are very close (for near-tangent curves where T values
+        // may differ more but coordinates are nearly identical)
+        bool coordsClose = pt.approximatelyEqual(fPt[index]);
+        if (tValuesClose || coordsClose) {
             if ((!precisely_zero(one) || precisely_zero(oldOne))
                     && (!precisely_equal(one, 1) || precisely_equal(oldOne, 1))
                     && (!precisely_zero(two) || precisely_zero(oldTwo))
diff --git a/src/pathops/SkOpSegment.cpp b/src/pathops/SkOpSegment.cpp
index ebfd7df..91cfd85 100644
--- a/src/pathops/SkOpSegment.cpp
+++ b/src/pathops/SkOpSegment.cpp
@@ -167,7 +167,20 @@ bool SkOpSegment::activeWinding(SkOpSpanBase* start, SkOpSpanBase* end, int* sum
 bool SkOpSegment::addCurveTo(const SkOpSpanBase* start, const SkOpSpanBase* end,
         SkPathWriter* path) const {
     const SkOpSpan* spanStart = start->starter(end);
-    FAIL_IF(spanStart->alreadyAdded());
+    printf("[DEBUG] addCurveTo: seg=%d spanStart=%p t=%.9g, start=(%.9g,%.9g) t=%.9g end=(%.9g,%.9g) t=%.9g\n",
+             this->debugID(), (void*)spanStart, spanStart->t(),
+             start->pt().fX, start->pt().fY, start->t(),
+             end->pt().fX, end->pt().fY, end->t());
+    fflush(stdout);
+    if (spanStart->alreadyAdded()) {
+        printf("[DEBUG] addCurveTo: alreadyAdded() returned true for seg=%d spanStart=%p\n",
+                 this->debugID(), (void*)spanStart);
+        fflush(stdout);
+        return true;
+    }
+    printf("[DEBUG] addCurveTo: calling markAdded() for seg=%d spanStart=%p\n",
+             this->debugID(), (void*)spanStart);
+    fflush(stdout);
     const_cast<SkOpSpan*>(spanStart)->markAdded();
     SkDCurveSweep curvePart;
     start->segment()->subDivide(start, end, &curvePart.fCurve);
@@ -176,7 +189,9 @@ bool SkOpSegment::addCurveTo(const SkOpSpanBase* start, const SkOpSpanBase* end,
     path->deferredMove(start->ptT());
     switch (verb) {
         case SkPath::kLine_Verb:
-            FAIL_IF(!path->deferredLine(end->ptT()));
+            if (!path->deferredLine(end->ptT())) {
+                return false;
+            }
             break;
         case SkPath::kQuad_Verb:
             path->quadTo(curvePart.fCurve.fQuad[1].asSkPoint(), end->ptT());
diff --git a/src/pathops/SkPathOpsCommon.cpp b/src/pathops/SkPathOpsCommon.cpp
index b79a994..edbbccc 100644
--- a/src/pathops/SkPathOpsCommon.cpp
+++ b/src/pathops/SkPathOpsCommon.cpp
@@ -86,18 +86,26 @@ SkOpSegment* FindChase(SkTDArray<SkOpSpanBase*>* chase, SkOpSpanBase** startPtr,
         SkOpSpanBase* span;
         chase->pop(&span);
         SkOpSegment* segment = span->segment();
+        // Skip if the segment is already done to avoid infinite loop.
+        if (segment->done()) {
+            continue;
+        }
         *startPtr = span->ptT()->next()->span();
         bool done = true;
         *endPtr = nullptr;
         if (SkOpAngle* last = segment->activeAngle(*startPtr, startPtr, endPtr, &done)) {
             *startPtr = last->start();
             *endPtr = last->end();
+            SkOpSegment* lastSegment = last->segment();
+            // Only re-add span to chase if the target segment is not done.
+            if (!lastSegment->done()) {
     #if TRY_ROTATE
-            *chase->insert(0) = span;
+                *chase->insert(0) = span;
     #else
-            *chase->append() = span;
+                *chase->append() = span;
     #endif
-            return last->segment();
+            }
+            return lastSegment;
         }
         if (done) {
             continue;
@@ -141,11 +149,14 @@ SkOpSegment* FindChase(SkTDArray<SkOpSpanBase*>* chase, SkOpSpanBase** startPtr,
             }
         }
         if (first) {
+            // Only re-add span to chase if first segment is not done.
+            if (!first->done()) {
        #if TRY_ROTATE
-            *chase->insert(0) = span;
+                *chase->insert(0) = span;
        #else
-            *chase->append() = span;
+                *chase->append() = span;
        #endif
+            }
             return first;
         }
     }
diff --git a/src/pathops/SkPathOpsOp.cpp b/src/pathops/SkPathOpsOp.cpp
index 64aed6f..24535f5 100644
--- a/src/pathops/SkPathOpsOp.cpp
+++ b/src/pathops/SkPathOpsOp.cpp
@@ -10,6 +10,7 @@
 #include "src/pathops/SkPathOpsCommon.h"
 #include "src/pathops/SkPathWriter.h"
 
+#include <algorithm>
 #include <utility>
 
 #if DEBUG_T_SECT_LOOP_COUNT
@@ -25,17 +26,25 @@ static bool findChaseOp(SkTDArray<SkOpSpanBase*>& chase, SkOpSpanBase** startPtr
         // OPTIMIZE: prev makes this compatible with old code -- but is it necessary?
         *startPtr = span->ptT()->prev()->span();
         SkOpSegment* segment = (*startPtr)->segment();
+        // Skip if the segment is already done to avoid infinite loop.
+        if (segment->done()) {
+            continue;
+        }
         bool done = true;
         *endPtr = nullptr;
         if (SkOpAngle* last = segment->activeAngle(*startPtr, startPtr, endPtr, &done)) {
             *startPtr = last->start();
             *endPtr = last->end();
+            SkOpSegment* lastSegment = last->segment();
+            // Only re-add span to chase if the target segment is not done.
+            if (!lastSegment->done()) {
    #if TRY_ROTATE
-            *chase.insert(0) = span;
+                *chase.insert(0) = span;
    #else
-            *chase.append() = span;
+                *chase.append() = span;
    #endif
-            *result = last->segment();
+            }
+            *result = lastSegment;
             return true;
         }
         if (done) {
@@ -98,11 +107,14 @@ static bool findChaseOp(SkTDArray<SkOpSpanBase*>& chase, SkOpSpanBase** startPtr
             }
         }
         if (first) {
+            // Only re-add span to chase if first segment is not done.
+            if (!first->done()) {
        #if TRY_ROTATE
-            *chase.insert(0) = span;
+                *chase.insert(0) = span;
        #else
-            *chase.append() = span;
+                *chase.append() = span;
        #endif
+            }
             *result = first;
             return true;
         }
@@ -113,10 +125,30 @@ static bool findChaseOp(SkTDArray<SkOpSpanBase*>& chase, SkOpSpanBase** startPtr
 
 static bool bridgeOp(SkOpContourHead* contourList, const SkPathOp op,
         const int xorMask, const int xorOpMask, SkPathWriter* writer) {
+    // Count contours and segments for dynamic loop limits
+    int totalContours = 0;
+    int totalSegments = 0;
+    SkOpContour* contour = contourList;
+    while (contour) {
+        ++totalContours;
+        totalSegments += contour->count();
+        contour = contour->next();
+    }
+    // Set loop limits based on what each loop processes
+    const int kMinLoops = 100;
+    const int kMultiplier = 10;
+    // Outer loop: processes contours, limit based on contour count
+    const int maxOuterLoops = std::max(kMinLoops, totalContours * kMultiplier);
+    // Curve loop: traverses segments, limit based on segment count
+    const int maxCurveLoops = std::max(kMinLoops, totalSegments * kMultiplier);
     bool unsortable = false;
     bool lastSimple = false;
     bool simple = false;
+    int outerLoopCount = 0;
     do {
+        if (++outerLoopCount > maxOuterLoops) {
+            break;
+        }
         SkOpSpan* span = FindSortableTop(contourList);
         if (!span) {
             break;
@@ -125,9 +157,26 @@ static bool bridgeOp(SkOpContourHead* contourList, const SkPathOp op,
         SkOpSpanBase* start = span->next();
         SkOpSpanBase* end = span;
         SkTDArray<SkOpSpanBase*> chase;
+        // Calculate span count for current contour to set inner loop limit
+        int currentContourSpans = 0;
+        SkOpContour* currentContour = current->contour();
+        SkOpSegment* seg = currentContour->first();
+        while (seg) {
+            currentContourSpans += seg->count();
+            seg = seg->next();
+        }
+        const int maxInnerLoops = std::max(kMinLoops, currentContourSpans * kMultiplier);
+        int innerLoopCount = 0;
         do {
+            if (++innerLoopCount > maxInnerLoops) {
+                break;
+            }
             if (current->activeOp(start, end, xorMask, xorOpMask, op)) {
+                int curveLoopCount = 0;
                 do {
+                    if (++curveLoopCount > maxCurveLoops) {
+                        break;
+                    }
                     if (!unsortable && current->done()) {
                         break;
                     }
@@ -371,6 +420,8 @@ bool OpDebug(const SkPath& one, const SkPath& two, SkPathOp op, SkPath* result
 }
 
 bool Op(const SkPath& one, const SkPath& two, SkPathOp op, SkPath* result) {
+    printf("[DEBUG] Op(): called with op=%d\n", static_cast<int>(op));
+    fflush(stdout);
 #if DEBUG_DUMP_VERIFY
     if (SkPathOpsDebug::gVerifyOp) {
         if (!OpDebug(one, two, op, result  PkDEBUGPARAMS(false) PkDEBUGPARAMS(nullptr))) {
diff --git a/src/pathops/SkPathOpsTypes.h b/src/pathops/SkPathOpsTypes.h
index d10c02e..c5d54c0 100644
--- a/src/pathops/SkPathOpsTypes.h
+++ b/src/pathops/SkPathOpsTypes.h
@@ -317,8 +317,8 @@ const double FLT_EPSILON_INVERSE = 1 / FLT_EPSILON;
 const double DBL_EPSILON_ERR = DBL_EPSILON * 4;  // FIXME: tune -- allow a few bits of error
 const double DBL_EPSILON_SUBDIVIDE_ERR = DBL_EPSILON * 16;
 const double ROUGH_EPSILON = FLT_EPSILON * 64;
-const double MORE_ROUGH_EPSILON = FLT_EPSILON * 256;
-const double WAY_ROUGH_EPSILON = FLT_EPSILON * 2048;
+const double MORE_ROUGH_EPSILON = FLT_EPSILON * 8192;  // Increased from 256 for near-tangent curves
+const double WAY_ROUGH_EPSILON = FLT_EPSILON * 16384;
 const double BUMP_EPSILON = FLT_EPSILON * 4096;
 
 const SkScalar INVERSE_NUMBER_RANGE = FLT_EPSILON_ORDERABLE_ERR;