diff --git a/data/core.yaml b/data/core.yaml
index f1450b43e..bace83675 100644
--- a/data/core.yaml
+++ b/data/core.yaml
@@ -55,6 +55,7 @@ en:
         line: Made a line circular.
         area: Made an area circular.
       not_closed: This can't be made circular because it's not a loop.
+      too_large: This can't be made circular because it extends too far beyond the viewable map.
     orthogonalize:
       title: Square
       description:
@@ -65,6 +66,7 @@ en:
         line: Squared the corners of a line.
         area: Squared the corners of an area.
       not_squarish: This can't be made square because it is not squarish.
+      too_large: This can't be made square because it extends too far beyond the viewable map.
     straighten:
       title: Straighten
       description: Straighten this line.
diff --git a/dist/locales/en.json b/dist/locales/en.json
index 240edfa6e..b5a466c9a 100644
--- a/dist/locales/en.json
+++ b/dist/locales/en.json
@@ -71,7 +71,8 @@
                 "line": "Made a line circular.",
                 "area": "Made an area circular."
             },
-            "not_closed": "This can't be made circular because it's not a loop."
+            "not_closed": "This can't be made circular because it's not a loop.",
+            "too_large": "This can't be made circular because not enough of it is currently visible."
         },
         "orthogonalize": {
             "title": "Square",
@@ -84,7 +85,8 @@
                 "line": "Squared the corners of a line.",
                 "area": "Squared the corners of an area."
             },
-            "not_squarish": "This can't be made square because it is not squarish."
+            "not_squarish": "This can't be made square because it is not squarish.",
+            "too_large": "This can't be made square because not enough of it is currently visible."
         },
         "straighten": {
             "title": "Straighten",
diff --git a/js/id/geo/extent.js b/js/id/geo/extent.js
index 189e03058..2081f82c2 100644
--- a/js/id/geo/extent.js
+++ b/js/id/geo/extent.js
@@ -22,6 +22,10 @@ _.extend(iD.geo.Extent.prototype, {
                               Math.max(obj[1][1], this[1][1])]);
     },
 
+    area: function() {
+        return Math.abs((this[1][0] - this[0][0]) * (this[1][1] - this[0][1]));
+    },
+
     center: function() {
         return [(this[0][0] + this[1][0]) / 2,
                 (this[0][1] + this[1][1]) / 2];
diff --git a/js/id/operations/circularize.js b/js/id/operations/circularize.js
index 4ec23d477..2e59b90e7 100644
--- a/js/id/operations/circularize.js
+++ b/js/id/operations/circularize.js
@@ -14,7 +14,17 @@ iD.operations.Circularize = function(selectedIDs, context) {
     };
 
     operation.disabled = function() {
-        return action.disabled(context.graph());
+        var way = context.entity(entityId),
+            wayExtent = way.extent(context.graph()),
+            mapExtent = context.extent(),
+            intersection = mapExtent.intersection(wayExtent),
+            pctVisible = intersection.area() / wayExtent.area();
+
+        if (pctVisible < 0.8) {
+            return 'too_large';
+        } else {
+            return action.disabled(context.graph());
+        }
     };
 
     operation.tooltip = function() {
diff --git a/js/id/operations/orthogonalize.js b/js/id/operations/orthogonalize.js
index 980d4d52d..e99827806 100644
--- a/js/id/operations/orthogonalize.js
+++ b/js/id/operations/orthogonalize.js
@@ -17,7 +17,17 @@ iD.operations.Orthogonalize = function(selectedIDs, context) {
     };
 
     operation.disabled = function() {
-        return action.disabled(context.graph());
+        var way = context.entity(entityId),
+            wayExtent = way.extent(context.graph()),
+            mapExtent = context.extent(),
+            intersection = mapExtent.intersection(wayExtent),
+            pctVisible = intersection.area() / wayExtent.area();
+
+        if (pctVisible < 0.8) {
+            return 'too_large';
+        } else {
+            return action.disabled(context.graph());
+        }
     };
 
     operation.tooltip = function() {
diff --git a/test/spec/geo/extent.js b/test/spec/geo/extent.js
index 66526c1b6..9ca751efc 100644
--- a/test/spec/geo/extent.js
+++ b/test/spec/geo/extent.js
@@ -51,6 +51,12 @@ describe("iD.geo.Extent", function () {
         });
     });
 
+    describe("#area", function () {
+        it("returns the area", function () {
+           expect(iD.geo.Extent([0, 0], [5, 10]).area()).to.eql(50);
+        });
+    });
+
     describe("#padByMeters", function () {
         it("does not change centerpoint of an extent", function () {
            var min = [0, 0], max = [5, 10];