diff --git a/src/arith/modular_set.cc b/src/arith/modular_set.cc
index f455695438ec..ac6bf94b1198 100644
--- a/src/arith/modular_set.cc
+++ b/src/arith/modular_set.cc
@@ -67,7 +67,18 @@ struct ModularSetAnalyzer::Entry {
   Entry() = default;
 
   Entry(int64_t coeff, int64_t base) {
-    ICHECK_GE(coeff, 0);
+    if (coeff < 0) {
+      // `analyzer->canonical_simplify()` can generate expressions with
+      // negative coefficients (e.g. simplifying `floormod(-i, 2)`
+      // into `floormod(i, -2) * -1`).  When this happens, the
+      // ModularSet may enter a constraint based on this expression.
+      //
+      // Handling a negative coeff uses the same sign convention as
+      // canonical_simplify, requiring that
+      // `floormod(var, coeff) == -floormod(var, -coeff)`.
+      coeff *= -1;
+      base *= -1;
+    }
     this->coeff = coeff;
     if (coeff != 0) {
       base = base % coeff;
diff --git a/tests/python/unittest/test_arith_canonical_simplify.py b/tests/python/unittest/test_arith_canonical_simplify.py
index 81a163d0d431..9f187685991e 100644
--- a/tests/python/unittest/test_arith_canonical_simplify.py
+++ b/tests/python/unittest/test_arith_canonical_simplify.py
@@ -97,6 +97,8 @@ def test_split_index_simplify():
     # cannot simplify mixed case, unless we canonicalize into one mode.
     ck.verify(tdiv(x, 6) * 2 + tmod(fld(x, 3), 2), tdiv(x, 6) * 2 + tmod(fld(x, 3), 2))
 
+    ck.verify(tmod(-x, 2), tmod(x, -2) * -1)
+
 
 def test_div_simplify():
     ck = CanonicalChecker()
@@ -129,6 +131,8 @@ def test_floormod_simplify():
     ck.verify(flm(flm((x * 4) + y - 466036, 24528) - 24512, 16), flm((x * 4) + y + 12, 16))
     ck.verify(flm(flm((x * 4), 16), 8), flm(x, 2) * 4)
 
+    ck.verify(flm(-x, 2), flm(x, -2) * -1)
+
 
 def test_canonical_mixed():
     ck = CanonicalChecker()
diff --git a/tests/python/unittest/test_tir_transform_simplify.py b/tests/python/unittest/test_tir_transform_simplify.py
index 2eb9c3546ee5..46b6858ec773 100644
--- a/tests/python/unittest/test_tir_transform_simplify.py
+++ b/tests/python/unittest/test_tir_transform_simplify.py
@@ -816,5 +816,34 @@ def expected(A: T.Buffer[1, "bool"], i: T.int32, j: T.int32, k: T.int32):
         A[0] = (i != 30) or (j == 0)
 
 
+class TestConditionalFloorMod(BaseBeforeAfter):
+    """A regression test for negative floormod denominator
+
+    Previously, simplifying this function could throw an error.  First, the
+    `canonical_simplify` would rewrite `floormod(0-i,2)` to the equivalent
+    `floormod(i,-2)`.  Then, the rewrite_simplifier would enter a
+    constrained context in which `floormod(i,-2)==1`.  Passing this
+    expression to `ModularSet::EnterConstraint`, which previously did not
+    support a negative value for the second argument, threw an error.
+
+    The analogous failure mode never occurred for `truncmod`, because
+    `truncmod(0-i,2)` would be canonicalized to `truncmod(i, -2) * -1`, and
+    the pattern matching in `ModularSet` didn't recognize the constant
+    factor.
+
+    This failure mode was resolved by supporting negative arguments in
+    `ModularSet`, using the same sign convention as is used by
+    `canonical_simplify`.
+    """
+
+    def before(A: T.Buffer[1, "bool"], i: T.int32):
+        if T.floormod(0 - i, 2) == 0:
+            A[0] = T.floormod(i, 2) == 0
+
+    def expected(A: T.Buffer[1, "bool"], i: T.int32):
+        if T.floormod(i, -2) == 0:
+            A[0] = True
+
+
 if __name__ == "__main__":
     tvm.testing.main()