diff --git a/docs/docs/configuration.md b/docs/docs/configuration.md
index 2ba8837844cb..aaec735d85a2 100644
--- a/docs/docs/configuration.md
+++ b/docs/docs/configuration.md
@@ -293,8 +293,9 @@ will not be rendered when in one of the excluded locations.
 ]
 ```
 
-You can also specify a [regular expression][regex] to create folder wildcards.
-In the sample below, any folders inside the `/Users/posh/Projects` path will be matched.
+The strings specified in these properties are evaluated as [regular expressions][regex]. You
+can use any valid regular expression construct, but the regular expression must match the entire directory
+name. The following will match `/Users/posh/Projects/Foo` but not `/home/Users/posh/Projects/Foo`.
 
 ```json
 "include_folders": [
@@ -313,16 +314,17 @@ You can also combine these properties:
 ]
 ```
 
-Note for Windows users: Windows directory separators should be specified as 4 backslashes.
+##### Notes
 
-```json
-"include_folders": [
-  "C:\\\\Projects.*"
-],
-"exclude_folders": [
-  "C:\\\\Projects\\\\secret-project.*"
-]
-```
+- Oh My Posh will accept both `/` and `\` as path separators for a folder and will match regardless of which
+is used by the current operating system.
+- Because the strings are evaluated as regular expressions, if you want to use a `\` in a Windows
+directory name, you need to specify it as `\\\\`.
+- The character `~` at the start of a specified folder will match the user's home directory.
+- The comparison is case-insensitive on Windows and macOS, but case-sensitive on other operating systems.
+
+This means that for user Bill, who has a user account `Bill` on Windows and `bill` on Linux,  `~/Foo` might match
+`C:\Users\Bill\Foo` or `C:\Users\Bill\foo` on Windows but only `/home/bill/Foo` on Linux.
 
 ### Colors
 
diff --git a/src/segment.go b/src/segment.go
index 012d885f8c3d..020c680de707 100644
--- a/src/segment.go
+++ b/src/segment.go
@@ -3,6 +3,7 @@ package main
 import (
 	"errors"
 	"fmt"
+	"strings"
 	"time"
 )
 
@@ -176,9 +177,20 @@ func (segment *Segment) cwdExcluded(cwd string) bool {
 }
 
 func (segment *Segment) cwdMatchesOneOf(cwd string, regexes []string) bool {
+	normalizedCwd := strings.ReplaceAll(cwd, "\\", "/")
+	normalizedHomeDir := strings.ReplaceAll(segment.env.homeDir(), "\\", "/")
+
 	for _, element := range regexes {
-		pattern := fmt.Sprintf("^%s$", element)
-		matched := matchString(pattern, cwd)
+		normalizedElement := strings.ReplaceAll(element, "\\\\", "/")
+		if strings.HasPrefix(normalizedElement, "~") {
+			normalizedElement = normalizedHomeDir + normalizedElement[1:]
+		}
+		pattern := fmt.Sprintf("^%s$", normalizedElement)
+		goos := segment.env.getRuntimeGOOS()
+		if goos == windowsPlatform || goos == darwinPlatform {
+			pattern = "(?i)" + pattern
+		}
+		matched := matchString(pattern, normalizedCwd)
 		if matched {
 			return true
 		}
diff --git a/src/segment_test.go b/src/segment_test.go
index 7765162db465..5cf71ae831a4 100644
--- a/src/segment_test.go
+++ b/src/segment_test.go
@@ -81,11 +81,15 @@ func TestShouldIncludeFolder(t *testing.T) {
 		{Case: "Include Mismatch / Exclude Mismatch", IncludeFolders: []string{"zProjects.*"}, ExcludeFolders: []string{"Projects/nope"}, Expected: false},
 	}
 	for _, tc := range cases {
+		env := new(MockedEnvironment)
+		env.On("getRuntimeGOOS", nil).Return(linuxPlatform)
+		env.On("homeDir", nil).Return("")
 		segment := &Segment{
 			Properties: map[Property]interface{}{
 				IncludeFolders: tc.IncludeFolders,
 				ExcludeFolders: tc.ExcludeFolders,
 			},
+			env: env,
 		}
 		got := segment.shouldIncludeFolder(cwd)
 		assert.Equal(t, tc.Expected, got, tc.Case)
@@ -93,10 +97,14 @@ func TestShouldIncludeFolder(t *testing.T) {
 }
 
 func TestShouldIncludeFolderRegexInverted(t *testing.T) {
+	env := new(MockedEnvironment)
+	env.On("getRuntimeGOOS", nil).Return(linuxPlatform)
+	env.On("homeDir", nil).Return("")
 	segment := &Segment{
 		Properties: map[Property]interface{}{
 			ExcludeFolders: []string{"(?!Projects[\\/]).*"},
 		},
+		env: env,
 	}
 	// detect panic(thrown by MustCompile)
 	defer func() {
@@ -109,10 +117,14 @@ func TestShouldIncludeFolderRegexInverted(t *testing.T) {
 }
 
 func TestShouldIncludeFolderRegexInvertedNonEscaped(t *testing.T) {
+	env := new(MockedEnvironment)
+	env.On("getRuntimeGOOS", nil).Return(linuxPlatform)
+	env.On("homeDir", nil).Return("")
 	segment := &Segment{
 		Properties: map[Property]interface{}{
 			ExcludeFolders: []string{"(?!Projects/).*"},
 		},
+		env: env,
 	}
 	// detect panic(thrown by MustCompile)
 	defer func() {
@@ -196,3 +208,39 @@ func TestGetColors(t *testing.T) {
 		assert.Equal(t, tc.ExpectedColor, color, tc.Case)
 	}
 }
+
+func TestCwdMatchesOneOf(t *testing.T) {
+	cases := []struct {
+		GOOS     string
+		HomeDir  string
+		Cwd      string
+		Pattern  string
+		Expected bool
+	}{
+		{GOOS: linuxPlatform, HomeDir: "/home/bill", Cwd: "/home/bill", Pattern: "/home/bill", Expected: true},
+		{GOOS: linuxPlatform, HomeDir: "/home/bill", Cwd: "/home/bill/foo", Pattern: "~/foo", Expected: true},
+		{GOOS: linuxPlatform, HomeDir: "/home/bill", Cwd: "/home/bill/foo", Pattern: "~/Foo", Expected: false},
+		{GOOS: linuxPlatform, HomeDir: "/home/bill", Cwd: "/home/bill/foo", Pattern: "~\\\\foo", Expected: true},
+		{GOOS: linuxPlatform, HomeDir: "/home/bill", Cwd: "/home/bill/foo/bar", Pattern: "~/fo.*", Expected: true},
+		{GOOS: linuxPlatform, HomeDir: "/home/bill", Cwd: "/home/bill/foo", Pattern: "~/fo\\w", Expected: true},
+		{GOOS: windowsPlatform, HomeDir: "C:\\Users\\Bill", Cwd: "C:\\Users\\Bill", Pattern: "C:\\\\Users\\\\Bill", Expected: true},
+		{GOOS: windowsPlatform, HomeDir: "C:\\Users\\Bill", Cwd: "C:\\Users\\Bill", Pattern: "C:/Users/Bill", Expected: true},
+		{GOOS: windowsPlatform, HomeDir: "C:\\Users\\Bill", Cwd: "C:\\Users\\Bill", Pattern: "c:/users/bill", Expected: true},
+		{GOOS: windowsPlatform, HomeDir: "C:\\Users\\Bill", Cwd: "C:\\Users\\Bill", Pattern: "~", Expected: true},
+		{GOOS: windowsPlatform, HomeDir: "C:\\Users\\Bill", Cwd: "C:\\Users\\Bill\\Foo", Pattern: "~/Foo", Expected: true},
+		{GOOS: windowsPlatform, HomeDir: "C:\\Users\\Bill", Cwd: "C:\\Users\\Bill\\Foo", Pattern: "~/foo", Expected: true},
+		{GOOS: windowsPlatform, HomeDir: "C:\\Users\\Bill", Cwd: "C:\\Users\\Bill\\Foo\\Bar", Pattern: "~/fo.*", Expected: true},
+		{GOOS: windowsPlatform, HomeDir: "C:\\Users\\Bill", Cwd: "C:\\Users\\Bill\\Foo", Pattern: "~/fo\\w", Expected: true},
+	}
+
+	for _, tc := range cases {
+		env := new(MockedEnvironment)
+		env.On("getRuntimeGOOS", nil).Return(tc.GOOS)
+		env.On("homeDir", nil).Return(tc.HomeDir)
+		segment := &Segment{
+			env: env,
+		}
+		got := segment.cwdMatchesOneOf(tc.Cwd, []string{tc.Pattern})
+		assert.Equal(t, tc.Expected, got)
+	}
+}