diff --git a/internal/manager/config/config.go b/internal/manager/config/config.go
index d8f1cf07..ba917785 100644
--- a/internal/manager/config/config.go
+++ b/internal/manager/config/config.go
@@ -443,7 +443,7 @@ func (c *Conf) ExpandVariables(inputChannel <-chan string, outputChannel chan<-
 			if !ok {
 				continue
 			}
-			if !strings.HasPrefix(expanded, managerValue) {
+			if !isValueMatch(expanded, managerValue) {
 				continue
 			}
 			expanded = targetValue + expanded[len(managerValue):]
@@ -484,7 +484,7 @@ func (c *Conf) ConvertTwoWayVariables(inputChannel <-chan string, outputChannel
 
 	doValueReplacement := func(valueToConvert string) string {
 		for varName, varValue := range twoWayVars {
-			if !strings.HasPrefix(valueToConvert, varValue) {
+			if !isValueMatch(valueToConvert, varValue) {
 				continue
 			}
 			valueToConvert = fmt.Sprintf("{%s}%s", varName, valueToConvert[len(varValue):])
@@ -498,6 +498,25 @@ func (c *Conf) ConvertTwoWayVariables(inputChannel <-chan string, outputChannel
 	}
 }
 
+// isValueMatch returns whether `valueToMatch` starts with `variableValue`.
+// When `variableValue` is a Windows path (with backslash separators), it is
+// also tested with forward slashes against `valueToMatch`.
+func isValueMatch(valueToMatch, variableValue string) bool {
+	if strings.HasPrefix(valueToMatch, variableValue) {
+		return true
+	}
+
+	// If the variable value has a backslash, assume it is a Windows path.
+	// Convert it to slash notation just to see if that would provide a
+	// match.
+	if strings.ContainsRune(variableValue, '\\') {
+		slashedValue := crosspath.ToSlash(variableValue)
+		return strings.HasPrefix(valueToMatch, slashedValue)
+	}
+
+	return false
+}
+
 // getVariables returns the variable values for this (audience, platform) combination.
 // If no variables are found, just returns an empty map. If a value is defined
 // for both the "all" platform and specifically the given platform, the specific
diff --git a/internal/manager/config/config_test.go b/internal/manager/config/config_test.go
index 9e38d320..95cb033d 100644
--- a/internal/manager/config/config_test.go
+++ b/internal/manager/config/config_test.go
@@ -18,3 +18,30 @@ func TestVariablesWithBackslashes(t *testing.T) {
 	assert.Equal(t, expectDouble, vars["double-backslash"]["blender"])
 	assert.Equal(t, expectSingle, vars["quoted-double-backslash"]["blender"])
 }
+
+func TestReplaceTwowayVariables(t *testing.T) {
+	c := DefaultConfig(func(c *Conf) {
+		c.Variables["shared"] = Variable{
+			IsTwoWay: true,
+			Values: []VariableValue{
+				{Value: "/shared/flamenco", Platform: VariablePlatformLinux},
+				{Value: `Y:\shared\flamenco`, Platform: VariablePlatformWindows},
+			},
+		}
+	})
+
+	feeder := make(chan string, 2)
+	receiver := make(chan string, 2)
+
+	feeder <- `Y:\shared\flamenco\shot\file.blend`
+
+	// This is the real reason for this test: forward slashes in the path should
+	// still be matched to the backslashes in the variable value.
+	feeder <- `Y:/shared/flamenco/shot/file.blend`
+	close(feeder)
+
+	c.ConvertTwoWayVariables(feeder, receiver, VariableAudienceUsers, VariablePlatformWindows)
+
+	assert.Equal(t, `{shared}\shot\file.blend`, <-receiver)
+	assert.Equal(t, `{shared}/shot/file.blend`, <-receiver)
+}