diff --git a/stdlib/public/core/Stride.swift b/stdlib/public/core/Stride.swift
index 9bfc6290fcadb..53e599b4eaaa2 100644
--- a/stdlib/public/core/Stride.swift
+++ b/stdlib/public/core/Stride.swift
@@ -215,14 +215,14 @@ public struct StrideToIterator<Element: Strideable> {
   internal let _stride: Element.Stride
 
   @usableFromInline
-  internal var _current: (index: Int?, value: Element)
+  internal var _current: (index: Int?, value: Element?)
 
   @inlinable
   internal init(_start: Element, end: Element, stride: Element.Stride) {
     self._start = _start
     _end = end
     _stride = stride
-    _current = (0, _start)
+    _current = (nil, nil)
   }
 }
 
@@ -233,12 +233,18 @@ extension StrideToIterator: IteratorProtocol {
   /// Once `nil` has been returned, all subsequent calls return `nil`.
   @inlinable
   public mutating func next() -> Element? {
-    let result = _current.value
-    if _stride > 0 ? result >= _end : result <= _end {
-      return nil
+    if let value = _current.value {
+      let deltaEnd = value.distance(to: _end)
+      if _stride > 0 ? deltaEnd > _stride : deltaEnd < _stride {
+        _current = Element._step(after: (_current.index, value), from: _start, by: _stride)
+      } else {
+        return nil
+      }
+    } else {
+      _current = (0, _start)
     }
-    _current = Element._step(after: _current, from: _start, by: _stride)
-    return result
+
+    return _current.value
   }
 }
 
@@ -416,7 +422,7 @@ public struct StrideThroughIterator<Element: Strideable> {
   internal let _stride: Element.Stride
 
   @usableFromInline
-  internal var _current: (index: Int?, value: Element)
+  internal var _current: (index: Int?, value: Element?)
 
   @usableFromInline
   internal var _didReturnEnd: Bool = false
@@ -426,7 +432,7 @@ public struct StrideThroughIterator<Element: Strideable> {
     self._start = _start
     _end = end
     _stride = stride
-    _current = (0, _start)
+    _current = (nil, nil)
   }
 }
 
@@ -437,19 +443,18 @@ extension StrideThroughIterator: IteratorProtocol {
   /// Once `nil` has been returned, all subsequent calls return `nil`.
   @inlinable
   public mutating func next() -> Element? {
-    let result = _current.value
-    if _stride > 0 ? result >= _end : result <= _end {
-      // This check is needed because if we just changed the above operators
-      // to > and <, respectively, we might advance current past the end
-      // and throw it out of bounds (e.g. above Int.max) unnecessarily.
-      if result == _end && !_didReturnEnd {
-        _didReturnEnd = true
-        return result
+    if let value = _current.value {
+      let deltaEnd = value.distance(to: _end)
+      if _stride > 0 ? deltaEnd >= self._stride : deltaEnd <= self._stride {
+        _current = Element._step(after: (_current.index, value), from: _start, by: _stride)
+      } else {
+        return nil
       }
-      return nil
+    } else {
+      _current = (0, _start)
     }
-    _current = Element._step(after: _current, from: _start, by: _stride)
-    return result
+
+    return _current.value
   }
 }
 
diff --git a/test/stdlib/Strideable.swift b/test/stdlib/Strideable.swift
index 91a2a83fa5343..16cef75674d86 100644
--- a/test/stdlib/Strideable.swift
+++ b/test/stdlib/Strideable.swift
@@ -61,6 +61,17 @@ struct R : Strideable {
   }
 }
 
+enum E : Int, Strideable {
+  case one = 1, two, three, four
+
+  func distance(to other: Self) -> Int {
+    return other.rawValue - self.rawValue
+  }
+  func advanced(by n: Int) -> Self {
+    return Self(rawValue: self.rawValue + n)!
+  }
+}
+
 StrideTestSuite.test("Double") {
   func checkOpen(from start: Double, to end: Double, by stepSize: Double, sum: Double) {
     // Work on Doubles
@@ -234,5 +245,20 @@ StrideTestSuite.test("StrideToIterator/past end/backward") {
   strideIteratorTest(stride(from: 3, to: 0, by: -1), nonNilResults: 3)
 }
 
+StrideTestSuite.test("UInt8") {
+  // SR-2016
+  strideIteratorTest(stride(from:253 as UInt8, to: 255, by: 2), nonNilResults: 1)
+  strideIteratorTest(stride(from:253 as UInt8, through: 255, by: 2), nonNilResults: 2)
+  strideIteratorTest(stride(from:2 as UInt8, to: 0, by: -2), nonNilResults: 1)
+  strideIteratorTest(stride(from:2 as UInt8, through: 0, by: -2), nonNilResults: 2)
+}
+
+StrideTestSuite.test("Enum") {
+  strideIteratorTest(stride(from:E.one as UInt8, to: E.four, by: 2), nonNilResults: 1)
+  strideIteratorTest(stride(from:E.one as UInt8, through: E.four, by: 2), nonNilResults: 2)
+  strideIteratorTest(stride(from:E.four as UInt8, to: E.one, by: -2), nonNilResults: 1)
+  strideIteratorTest(stride(from:E.four UInt8, through: E.one, by: -2), nonNilResults: 2)
+}
+
 runAllTests()