diff --git a/coderd/database/databasefake/databasefake.go b/coderd/database/databasefake/databasefake.go
index f0cdee99f2..839633f7f8 100644
--- a/coderd/database/databasefake/databasefake.go
+++ b/coderd/database/databasefake/databasefake.go
@@ -311,7 +311,7 @@ func (q *fakeQuerier) GetUserByEmailOrUsername(_ context.Context, arg database.G
 	defer q.mutex.RUnlock()
 
 	for _, user := range q.users {
-		if (user.Email == arg.Email || user.Username == arg.Username) && user.Deleted == arg.Deleted {
+		if (strings.EqualFold(user.Email, arg.Email) || strings.EqualFold(user.Username, arg.Username)) && user.Deleted == arg.Deleted {
 			return user, nil
 		}
 	}
diff --git a/coderd/database/dump.sql b/coderd/database/dump.sql
index 6bf0961b37..9413e0822d 100644
--- a/coderd/database/dump.sql
+++ b/coderd/database/dump.sql
@@ -532,6 +532,8 @@ CREATE UNIQUE INDEX idx_users_username ON users USING btree (username) WHERE (de
 
 CREATE UNIQUE INDEX templates_organization_id_name_idx ON templates USING btree (organization_id, lower((name)::text)) WHERE (deleted = false);
 
+CREATE UNIQUE INDEX users_email_lower_idx ON users USING btree (lower(email)) WHERE (deleted = false);
+
 CREATE UNIQUE INDEX users_username_lower_idx ON users USING btree (lower(username)) WHERE (deleted = false);
 
 CREATE UNIQUE INDEX workspaces_owner_id_lower_idx ON workspaces USING btree (owner_id, lower((name)::text)) WHERE (deleted = false);
diff --git a/coderd/database/migrations/000054_email_case.down.sql b/coderd/database/migrations/000054_email_case.down.sql
new file mode 100644
index 0000000000..e69de29bb2
diff --git a/coderd/database/migrations/000054_email_case.up.sql b/coderd/database/migrations/000054_email_case.up.sql
new file mode 100644
index 0000000000..90a80e550a
--- /dev/null
+++ b/coderd/database/migrations/000054_email_case.up.sql
@@ -0,0 +1 @@
+CREATE UNIQUE INDEX IF NOT EXISTS users_email_lower_idx ON users USING btree (lower(email)) WHERE (deleted = false);
diff --git a/coderd/database/queries.sql.go b/coderd/database/queries.sql.go
index ae7b420a05..669a9d2e07 100644
--- a/coderd/database/queries.sql.go
+++ b/coderd/database/queries.sql.go
@@ -3071,7 +3071,7 @@ SELECT
 FROM
 	users
 WHERE
-	(LOWER(username) = LOWER($1) OR email = $2)
+	(LOWER(username) = LOWER($1) OR LOWER(email) = LOWER($2))
 	AND deleted = $3
 LIMIT
 	1
diff --git a/coderd/database/queries/users.sql b/coderd/database/queries/users.sql
index fd47afa1a1..8f29e8a8d2 100644
--- a/coderd/database/queries/users.sql
+++ b/coderd/database/queries/users.sql
@@ -17,7 +17,7 @@ SELECT
 FROM
 	users
 WHERE
-	(LOWER(username) = LOWER(@username) OR email = @email)
+	(LOWER(username) = LOWER(@username) OR LOWER(email) = LOWER(@email))
 	AND deleted = @deleted
 LIMIT
 	1;
diff --git a/coderd/database/unique_constraint.go b/coderd/database/unique_constraint.go
index d3b38a8161..e0f8dfb9cd 100644
--- a/coderd/database/unique_constraint.go
+++ b/coderd/database/unique_constraint.go
@@ -20,6 +20,7 @@ const (
 	UniqueIndexUsersEmail                          UniqueConstraint = "idx_users_email"                                // CREATE UNIQUE INDEX idx_users_email ON users USING btree (email) WHERE (deleted = false);
 	UniqueIndexUsersUsername                       UniqueConstraint = "idx_users_username"                             // CREATE UNIQUE INDEX idx_users_username ON users USING btree (username) WHERE (deleted = false);
 	UniqueTemplatesOrganizationIDNameIndex         UniqueConstraint = "templates_organization_id_name_idx"             // CREATE UNIQUE INDEX templates_organization_id_name_idx ON templates USING btree (organization_id, lower((name)::text)) WHERE (deleted = false);
+	UniqueUsersEmailLowerIndex                     UniqueConstraint = "users_email_lower_idx"                          // CREATE UNIQUE INDEX users_email_lower_idx ON users USING btree (lower(email)) WHERE (deleted = false);
 	UniqueUsersUsernameLowerIndex                  UniqueConstraint = "users_username_lower_idx"                       // CREATE UNIQUE INDEX users_username_lower_idx ON users USING btree (lower(username)) WHERE (deleted = false);
 	UniqueWorkspacesOwnerIDLowerIndex              UniqueConstraint = "workspaces_owner_id_lower_idx"                  // CREATE UNIQUE INDEX workspaces_owner_id_lower_idx ON workspaces USING btree (owner_id, lower((name)::text)) WHERE (deleted = false);
 )
diff --git a/coderd/users_test.go b/coderd/users_test.go
index 6477b69113..e6c8d5da26 100644
--- a/coderd/users_test.go
+++ b/coderd/users_test.go
@@ -256,11 +256,19 @@ func TestPostLogin(t *testing.T) {
 		}
 		_, err := client.CreateFirstUser(ctx, req)
 		require.NoError(t, err)
+
 		_, err = client.LoginWithPassword(ctx, codersdk.LoginWithPasswordRequest{
 			Email:    req.Email,
 			Password: req.Password,
 		})
 		require.NoError(t, err)
+
+		// Login should be case insensitive
+		_, err = client.LoginWithPassword(ctx, codersdk.LoginWithPasswordRequest{
+			Email:    strings.ToUpper(req.Email),
+			Password: req.Password,
+		})
+		require.NoError(t, err)
 	})
 
 	t.Run("Lifetime&Expire", func(t *testing.T) {