The lemma I have attempted to prove is somewhat well known I think:
$a | b {\rm \: \Rightarrow \:}\phi(a) | \phi(b)$ (1)
$\phi(a) | \phi(b) {\rm \: \not\Rightarrow \:}a | b$ (2)
And in as much as I am sure there are proofs that are much shorter than my attempt, I wanted to try and do this keeping to elementary facts rather than restrict the proof to a particular domain of the naturals.Below is my attempt thus far, and below that is the part I have identified that still requires a vigorous proof in the context of my answer. This missing part applies to only to the proof of (1).
for (1) we have:
$a | b{\rm \: \Rightarrow \:} {rad(a)} |\, {rad(b)}$
${rad(a)} |\, {rad(b)}{\rm \: \Rightarrow \:}\prod_{p|a} p \, | \prod_{p|b} p$
$\prod_{p|a} p \, | \prod_{p|b} p{\rm \: \Rightarrow \:}\prod_{p|a} \Bigl(1-\frac{1}{p}\Bigr) | \,b\cdot \prod_{p|b} \Bigl(1-\frac{1}{p}\Bigr)$
$\prod_{p|a} \Bigl(1-\frac{1}{p}\Bigr) | \,b\cdot \prod_{p|b} \Bigl(1-\frac{1}{p}\Bigr){\rm \: \Rightarrow \:}{\Biggl\{\frac{b \cdot \prod_{p|b} (1-\frac{1}{p})}{\prod_{p|a} (1-\frac{1}{p})}}\Biggr\}=0$
${\Biggl\{\frac{b \cdot\prod_{p|b} (1-\frac{1}{p})}{\prod_{p|a} (1-\frac{1}{p})}}\Biggr\}=0 \land {\Bigl\{\frac{b}{a}}\Bigr\}=0{\rm \: \Rightarrow \:}{\Biggl\{\frac{b\prod_{p|b} (1-\frac{1}{p})}{a\prod_{p|a} (1-\frac{1}{p})}}\Biggr\}=0$
${\Biggl\{\frac{b\prod_{p|b} (1-\frac{1}{p})}{a\prod_{p|a} (1-\frac{1}{p})}}\Biggr\}=0{\rm \: \Rightarrow \:}{\Bigl\{\frac{\phi(b)}{\phi(a)}}\Bigr\}=0$
${\Bigl\{\frac{\phi(b)}{\phi(a)}}\Bigr\}=0{\rm \: \Rightarrow \:}\phi(a) | \phi(b)$
Thus establishing $a | b {\rm \: \Rightarrow \:}\phi(a) | \phi(b)$ is true.
We now look to establishing that (2) is true:
$\phi(a) | \phi(b) {\rm \: \Rightarrow \:}{\Bigl\{\frac{\phi(b)}{\phi(a)}}\Bigr\}=0$
${\Bigl\{\frac{\phi(b)}{\phi(a)}}\Bigr\}=0{\rm \: \Rightarrow \:}{\Bigl\{\frac{b}{a}}\Bigr\}=0 \lor {\Biggl\{\frac{\prod_{p|b} (1-\frac{1}{p})}{\prod_{p|a} (1-\frac{1}{p})}}\Biggr\}=0 \lor {\Biggl\{\frac{b}{\prod_{p|a} (1-\frac{1}{p})}}\Biggr\}=0$
Consider $z_1=x_1 y_1 \land z_2=x_2 y_2$ and $x_1,x_2,y_1,y_2 \in \mathbb Q$
And suppose we can assert ${\Biggl\{\frac{z_1}{z_2}}\Biggr\}=0$ knowing $z_2$ to divide $z_1$.
We then consider the individual divisibility criteria between the four integer variables in such a ratio with no remainder, as to allow us to see that the reason for the converse of (1) having a false truth value is elementary in nature, by finally substituting these generic variables for the four arithmetic functions appropriate in the division of the totients of $a$ and $b$, allowing us to see that either $a | b$ or it's negation can be true when only knowing $\phi(a) | \phi(b)$.
$\frac{x_2}{x_1} | \frac{ y_2}{ y_1}{\rm \: \Rightarrow \:}{\Biggl\{\frac{x_2}{x_1}}\Biggr\}=0 \land {\Biggl\{\frac{ y_2}{ y_1}}\Biggr\}=0{\rm \: \Rightarrow \:}{\Biggl\{\frac{x_1 y_1}{x_2 y_2}}\Biggr\}=0$
$\frac{x_2}{y_1} | \frac{ y_2}{ x_1}{\rm \: \Rightarrow \:}{\Biggl\{\frac{x_2}{y_1}}\Biggr\}=0 \land {\Biggl\{\frac{ y_2}{ x_1}}\Biggr\}=0{\rm \: \Rightarrow \:}{\Biggl\{\frac{x_1 y_1}{x_2 y_2}}\Biggr\}=0$
$\frac{x_2 y_2}{y_1} | {x_1}{\rm \: \Rightarrow \:}{\Biggl\{\frac{x_2 y_2}{y_1}}\Biggr\}=0 \land {\Biggl\{{ x_1}}\Biggr\}=0{\rm \: \Rightarrow \:}{\Biggl\{\frac{x_1 y_1}{x_2 y_2}}\Biggr\}=0$
$\frac{x_2 y_2}{x_1} | {y_1}{\rm \: \Rightarrow \:}{\Biggl\{\frac{x_2 y_2}{x_1}}\Biggr\}=0 \land {\Biggl\{{ y_1}}\Biggr\}=0 {\rm \: \Rightarrow \:}{\Biggl\{\frac{x_1 y_1}{x_2 y_2}}\Biggr\}=0$
Therefore:
${\Biggl\{\frac{z_1}{z_2}}\Biggr\}=0{\rm \: \Rightarrow \:}\frac{x_2}{x_1} | \frac{ y_2}{ y_1} \lor \frac{x_2}{y_1} | \frac{ y_2}{ x_1} \lor \frac{x_2 y_2}{y_1} | {x_1} \lor \frac{x_2 y_2}{x_1} | {y_1}$
Thus:
${\Bigl\{\frac{z_1}{z_2}}\Bigr\}=0{\rm \: \Rightarrow \:}S$
$S:({\Bigl\{\frac{ y_2}{ y_1}}\Bigr\}=0 \land {\Bigl\{\frac{x_1}{x_2}}\Bigr\}=0)\lor({\Bigl\{\frac{x_2}{y_1}}\Bigr\}=0 \land {\Bigl\{\frac{ y_2}{ x_1}}\Bigr\}=0)\lor({\Bigl\{\frac{x_2 y_2}{y_1}}\Bigr\}=0)\lor({\Bigl\{\frac{x_2 y_2}{x_1}}\Bigr\}=0)$
Then finally we make the substitutions as follows:
$$x_1=b$$ $$x_2=a$$ $$y_1=\prod_{p|b} (1-\frac{1}{p})$$ $$y_2=\prod_{p|a} (1-\frac{1}{p})$$
$\phi(a) | \phi(b){\rm \: \Rightarrow \:}{\Bigl\{\frac{\phi(b)}{\phi(a)}}\Bigr\}=0{\rm \: \Rightarrow \:}S_{\phi(a),\phi(b)}$
$S_{\phi(a),\phi(b)}:S_{\phi(a),\phi(b),1}\lor S_{\phi(a),\phi(b),2}\lor S_{\phi(a),\phi(b),3} \lor S_{\phi(a),\phi(b),4}$
Where:
$S_{\phi(a),\phi(b),1}:{\Bigl\{\frac{ \prod_{p|a} (1-\frac{1}{p})}{\prod_{p|b} (1-\frac{1}{p})}}\Bigr\}=0 \land {\Bigl\{\frac{b}{a}}\Bigr\}=0$
$S_{\phi(a),\phi(b),2}:{\Bigl\{\frac{a}{\prod_{p|b} (1-\frac{1}{p})}}\Bigr\}=0 \land {\Bigl\{\frac{ \prod_{p|a} (1-\frac{1}{p})}{ b}}\Bigr\}=0$
$S_{\phi(a),\phi(b),3}:{\Bigl\{\frac{a \prod_{p|a} (1-\frac{1}{p})}{\prod_{p|b} (1-\frac{1}{p})}}\Bigr\}=0$
$S_{\phi(a),\phi(b),4}:{\Bigl\{\frac{a \prod_{p|a} (1-\frac{1}{p})}{b}}\Bigr\}=0$
And finally it is clear that:
$S_{\phi(a),\phi(b)}{\rm \: \Rightarrow \:} a | b \lor \lnot(a | b)$
Therefore:
$\phi(a) | \phi(b) {\rm \: \not\Rightarrow \:}a | b$
MISSING PART: Show that:
$\Biggl(\prod_{p|a} \Bigl(1-\frac{1}{p}\Bigr) | \,b\cdot \prod_{p|b} \Bigl(1-\frac{1}{p}\Bigr) \Biggr)$
is true $\forall a,b \in \mathbb N$ such that $a |b$
Case 1:
$\lnot \Biggl(\prod_{p|a} \Bigl(1-\frac{1}{p}\Bigr) | \,b \Biggr)\land \lnot\Biggl(\prod_{p|a} \Bigl(1-\frac{1}{p}\Bigr) | \prod_{p|b} \Bigl(1-\frac{1}{p}\Bigr) \Biggr)$
Case 2:
$\Biggl(\prod_{p|a} \Bigl(1-\frac{1}{p}\Bigr) | \,b \Biggr)\land \lnot\Biggl(\prod_{p|a} \Bigl(1-\frac{1}{p}\Bigr) | \prod_{p|b} \Bigl(1-\frac{1}{p}\Bigr) \Biggr)$
Case 3:
$\lnot \Biggl(\prod_{p|a} \Bigl(1-\frac{1}{p}\Bigr) | \,b \Biggr)\land \Biggl(\prod_{p|a} \Bigl(1-\frac{1}{p}\Bigr) | \prod_{p|b} \Bigl(1-\frac{1}{p}\Bigr) \Biggr)$
I would suggest the following proof of $$a|b\implies \phi(a)|\phi(b)$$
First of all, as you did , we notice $$a|b\implies rad(a)|rad(b)$$
So, there exists a positive integer $k$ with $$k\cdot rad(a)=rad(b)$$
$k$ and $rad(a)$ must be coprime, otherwise the left side would not be squarefree, but the rightside is. Hence, we have $$\phi(rad(b))=\phi(k)\cdot \phi(rad(a))$$ Therefore $$\phi(rad(a))|\phi(rad(b))$$
So we get $$\phi(a)=a\cdot \phi(rad(a))|b\cdot \phi(rad(b))=\phi(b)$$